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Woolston, Christopher Richard Joseph. "The spectral and biological properties of some substituted 1,3-thiazolidin-4-ones." Thesis, University of Hertfordshire, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.254661.
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Revelant, Germain. "Conception, Synthèse et Évaluation Biologique d'Hétéroarylimino-1,3-thiazolidin-4-ones à Activité anti-cancéreuse potentielle." Thesis, Université de Lorraine, 2012. http://www.theses.fr/2012LORR0078/document.
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Le cancer, première cause de mortalité dans les pays développés, est une maladie aux origines diverses, caractérisée par une prolifération anarchique de cellules anormales. Celle-ci est principalement causée par un déréglement du cycle cellulaire, qui assure en temps normal le renouvellement des cellules de l?organisme. De nombreuses thérapies sont actuellement utilisées afin de lutter contre cette maladie, mais leurs effets secondaires importants incitent à développer de nouveaux composés antitumoraux. Parmi ceux-ci, les dérivés de thiazolidinones apparaissent comme particulièrement intéressants, notamment du fait de la variété des cibles qu?ils semblent pouvoir atteindre. Nous avons donc réalisé la conception, la synthèse et l?évaluation biologique de nouvelles séries de 2-iminothiazolidinones fonctionnalisées, à partir de composés hétérocycliques dont nous avons l?expérience au laboratoire (thiophène, sélénophène, thiazole), mais aussi de nouveaux précurseurs dont nous avons mis au point la synthèse au cours de nos travaux. La détermination du potentiel antiprolifératif de ces composés a permis d'isoler plusieurs structures prometteuses, présentant des IC50 de l?ordre du micromolaire sur les lignées cellulaires étudiées, et dont l'activité pourrait être liée à une capacité inhibitrice des phosphatases CDC25, principales régulatrices de la progression du cycle cellulaire<br>Cancer, which is the first cause of death care in developed countries, is a disease from various origins, and characterized by an uncontrolled proliferation of abnormal cells. This proliferation is mainly caused by a deregulation of the cell cycle, which usually provides the renewal of the organism cells. Many treatments are currently used to fight this disease, but showing important adverse effects. For this reason, the development of new antitumor compounds appears as a major challenge in medicinal chemistry. Among the investigated compounds, thiazolidinone derivatives appear as particularly interesting, especially due to the variety of targets they are described to interact with.Thus, we performed the design, synthesis and biological evaluation of new series of variously functionalized 2-iminothiazolidinones, starting from heterocycles already investigated in the laboratory (thiophene, selenophene, thiazole), but also from new precursors developed during our investigations. Determination of the antiproliferative activity of those compounds allowed to isolate some promising structures, showing IC50 values in micromolar range on investigated cell lines, maybe due to the inhibition of CDC25 phosphatases, which are responsible of the cell cycle regulation
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Abdillahi, Ismail. "Synthèse des pyrimidinones, des 1,3-thiazolidin-4-ones et des thiéno [3,2-d] [1,3] thiazoles à partir d'analogues thiophéniques d'acide anthranilique." Thesis, Metz, 2011. http://www.theses.fr/2011METZ003S/document.
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Dans le cadre de recherches sur les analogues thiophéniques de l’acide anthranilique, nous avons préparé ceux-ci soit au départ de béta-chloroacrylonitriles par une suite de condensation et de cyclisation, soit à partir de dérivés cétoniques en utilisant la méthode de Gewald. L’accès aux béta-chloroacrylonitriles béta-substitués utilise une séquence réactionnelle développée au laboratoire. Nous avons ensuite utilisé la présence de fonction amine ou acide (sous forme d’ester) pour la synthèse des systèmes condensés tels les pyrimidinones par condensation avec le chlorhydrate de chloroformamide, lactames ou o-phénylènediamine. La possibilité d’accès à partir des dérivés amino-ester aux dérivés aminés nous a permis la construction de nouveaux systèmes hétérocycliques substituant du noyau thiophénique tels les 2-chloro N-(3-thiényl) acétamides, isothiocyanates et N-(3-thiényl) thio-urée, utilisés pour la synthèse des systèmes condensés tels les 1,3-thiazolidinones et les thiéno[3,2-d][1,3]thiazoles<br>We prepared thiophene analogues of anthranilic acid starting either from béta-chloroacrylonitrile followed (by condensation and cyclisation) or from ketone derivatives (Gewald’s method).Acces to b-substituted b-chloroacrylonitriles was done using a pathway developed in the laboratory.Those o-amino ester compounds allowed the synthesis of condensed thiophenes like thiopyrimidinones via with chloroformamide hydrochloride, lactams or o-phenylenediamine.Saponification followed by decarboxylation of the same o-amino ester thiophenes led to 3-NH2-thiophenes. Conversation in 2-Cl-N-3-thienyl acetamids, isothiocyanates and N-3-thienyl thiouea and their subsequent transformation gave new heterocyclic scaffold: 1,3-thiozolidinones and thieno[3,2-d][1,3]thiazoles
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Sarkis, Manal. "Les phosphates CDC25 constituent-elles des cibles importantes en cancérologie : Des inhibiteurs de l'activité enzymatique vers les inhibiteurs de l'interaction entre CDC25 et leurs substrats CDK-Cycline." Thesis, Paris 5, 2012. http://www.theses.fr/2012PA05P635.
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Les phosphatases CDC25 sont des éléments-clé de la régulation du cycle cellulaire chez les eucaryotes; elles activent par une double déphosphorylation les complexes CDK/cyclines permettant ainsi la progression dans les différentes phases du cycle. Leur sur-expression, observée dans des cancers très fréquents, est corrélée à une forte agressivité des tumeurs et un mauvais pronostic ce qui en fait des cibles d’intérêt en cancérologie. Deux nouvelles séries d’inhibiteurs ont été développées à partir d’une thiazolopyrimidinone (TZP), capable d’inhiber l’activité des CDC25, et préalablement identifiée par l’équipe. La première série a été obtenue par dimérisation de deux noyaux thiazolones conduisant à des inhibiteurs avec des CI50 de l’ordre du micromolaire sur CDC25B plus actifs que les mono-thiazolones, ces composés étant sélectifs vs PTP1B et VHR. De plus, ces dimères semblent interagir avec le site actif et la poche de liaison des inhibiteurs. Une deuxième série d’analogues de thiazolidin-4-one a été obtenue par simplification de la structure TZP. Une réaction à quatre composants, utilisant l’énergie micro-onde, a été développée pour préparer rapidement des inhibiteurs de CDC25B avec des CI50 de l’ordre du micromolaire. Enfin, une approche originale pour inhiber CDC25 en ciblant l’interaction CDC25/CDK-Cycline a débutée. Un crible in silico/in vitro sera réalisé afin d’identifier de petites molécules inhibitrices de cette interaction. Des études préliminaires pour la mise en place d’outils permettant l’évaluation de l’affinité de ces molécules pour le site de reconnaissance de CDK2 ont été engagées<br>CDC25 phosphatases are key regulators of the cell cycle and its checkpoints. Hence, they are required to dephosphorylate and thus activate the Cdk/Cyclin complexes triggering progression through the different phases. Over-expression of CDC25 has been demonstrated in a large number of human tumors and is often associated with aggressiveness and poor clinical prognosis. CDC25 phosphatases may therefore represent attractive targets for anti-cancer therapy. Starting from a thiazolopyrimidinone (TZP) structure, previously reported as CDC25 inhibitor in our laboratory, two series of new compounds have been developed. Dimerisation of the thiazolone scaffold led to bis-thiazolone derivatives with inhibitory activities in the micromolar range greater than that observed for the mono-thiazolones. Moreover, most of these compounds were selective CDC25 inhibitors. A second scaffold was designed by opening of the pyrimidine ring of the TZP, leading to thiazolidine-4-one derivatives that inhibit CDC25B activities with values of IC50 in the micromolar range. A four-component reaction, using micro-wave irradiation, was developed to rapidly prepare these compounds. Finally, an approach aiming at inhibiting the interactions between phosphatase CDC25 and its substrate CDK2 was engaged. Several virtual chemical libraries will be screened in silico, and the small molecules candidates selected will be assessed for their binding affinity using an in vitro assay, that we sought to develop
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Smetanin, Vadim. "3-amino-2-tiokso-tizolidin-4-ono darinių sintezė ir jų antimikrobinio poveikio įvertinimas." Master's thesis, Lithuanian Academic Libraries Network (LABT), 2014. http://vddb.library.lt/obj/LT-eLABa-0001:E.02~2014~D_20140618_233456-51435.
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Darbo tikslas: susintetinti 3-amino rodanino pagrindą turinčius junginius ir nustatyti jų antimikrobinį aktyvumą.
Uždaviniai: 1) Sintezuoti 3-amiono-2-tiokso-4-tiazolidinono darinius; 2) Įvertinti gautų junginių antimikrobinį aktyvumą, naudojant in silico PASS online. 3) Įvertinti gautų junginių antimikrobinį aktyvumą in vitro standžioje terpėje; 4) Susieti junginių struktūrą su antimikrobiniu aktyvumu.
Tyrimo metodai: sintetintų junginių antimikrobinis poveikis buvo prognozuojamas „PASS online“ programos pagalba. Antimikrobinis aktyvumas tirtas in vitro, naudojant Miulerio – Hintono agarą. Atlikti ESC tyrimai junginių grynumui nustatyti ir FT-IR tyrimai junginių struktūrai patvirtinti.
Tyrimo rezultatai: 3-aminorodanino pagrindu buvo sintetinti 7 junginiai, turintys Šifo bazės struktūrą ir 1 turintis azetidino funkcinę grupę. Atlikti junginių lydymosi temperatūros nustatymo tyrimai, grynumas nustatytas naudojant ESC, junginių struktūra patvirtinta naudojant FTIR metodiką. PASS online programos pagalba buvo nustatyta, kad dauguma junginių turį potencialų antimikrobinį poveikį. Antimikrobinio poveikio in vitro tyrimo metu buvo nustatyta, kad plačiausią poveikį turi junginys VS-3, turintis p-chlorbenzaldehido pakaitą, ir VS-2, turintis p-brombenzaldehido pakaitą. Taip pat nustatyta, kad ribotu antimikrobiniu aktyvumu pasižymėjo junginiai VS-6, VS-7, VS-8. Įterpus azetidino struktūrą į VS-1 junginį, aktyvumas padidėjo Candida grybelių atžvilgiu.
Išvados: iš sintetintų junginių... [toliau žr. visą tekstą]<br>The aim of the research: Synthesis of 3-aminorhodanine derivatives, antimicrobial evaluation. Methods: Antimicrobial activity of synthesized 3-aminorhodanine derivatives was predicted with the help of PASS online program. Factual antimicrobial activity of compounds was determined using in vitro agar method. The purity and structure of compounds was analyzed with ESC and FT-IR methods accordingly. Results: 7 Schiff base derivatives and one azetidine compound were synthesized on the base of 3-aminorhodonine. The melting points were identified, the purity of compounds were determined using ESC, the compound structure was identified using FTIR. Analyzing the compounds with PASS online showed that most of the compounds possess the potential of antimicrobial activity. In vitro antimicrobial studies showed that the widest spectrum of activity was possessed by compound VS-3, which had the 4-chlorbenzaldehyde moiety, and VS-2 with 4-bromobenzaldehyde moiety. Compounds VS-6, VS-7 and VS-8 showed limited antimicrobial activity. Modifying VS-1 structure by adding an azotidine moiety increased the drugs effect on Candida fungi family. Conclusion: amongst all the synthesized compounds 3-(4-chlorophenyl)methyleneamino]-2-thioxo-thiazolidin-4-one and 3-(4-bromphenyl)methyleneamino]-2-thioxo-thiazolidin-4-one showed most antimicrobial promise.
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Fresneau, Patrick. "Inhibiteurs de l'aldose-réductase de structure imidazolidine / thiazolidine-acétique : synthèse, activités inhibitrices, relations structure activité quantitatives et modélisation moléculaire." Université Joseph Fourier (Grenoble), 1996. http://www.theses.fr/1996GRE18007.
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Nicolle, Edwige. "Nouvelles thiazolidino [3,2-a] pyrimidines : synthèse, étude structurale et pharmacologique." Université Joseph Fourier (Grenoble), 1990. http://www.theses.fr/1990GRE18007.
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Duflocq, Stéphane. "Conception et évaluation de peptides inhibiteurs de l'interaction ribosomale hCINAP/RPS14 dans un but antitumoral." Thesis, Université Paris Cité, 2021. http://www.theses.fr/2021UNIP5041.
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En réponse à différents stress, la protéine p53 est activée afin de promouvoir des changements de métabolisme, l'arrêt du cycle cellulaire et la réparation de l'ADN. En cas de trop fortes mutations, cette protéine peut aussi entraîner l'autodestruction de la cellule. Ce mécanisme de mort cellulaire programmée, appelé apoptose, s'opère naturellement dès le stade embryonnaire et permet de réguler le stock cellulaire. Ce rôle essentiel est néanmoins inactivé dans les cellules cancéreuses où dans la moitié des cas, p53 est mutée. La protéine HDM2 entraîne la dégradation de p53 par ubiquitinylation permettant ainsi aux cellules cancéreuses d'échapper à ce contrôle malgré leur forte dégénérescence. L'inhibition à différents niveaux de la biogenèse des ribosomes conduit à la stabilisation et à l'accumulation de p53. Ce processus finement régulé fait appel à près de 200 facteurs d'assemblage, dont hCINAP. Celui-ci entre notamment en interaction avec la protéine ribosomale RPS14 durant la dernière étape de maturation de la petite sous-unité ribosomique. Seule, RPS14 a la propriété de se lier à HMD2 et de lever l'inhibition de p53. L'objectif de cette thèse repose sur la synthèse chimique d'inhibiteurs peptidiques ciblant l'interaction hCINAP/RPS14 dans le but de restaurer l'activité de p53 et de perturber la biogenèse des ribosomes entraînant un double effet antitumoral. Ce travail s'appuie sur une structure cristallographique de Fap7, homologue archée de hCINAP, en complexe avec RPS14. En mimant la boucle C-terminale de RPS14, ces peptides cycliques innovants ont pour but de promouvoir la liaison RPS14/HDM2. Des méthodes de ligation peptidiques portant sur le noyau thiazolidine pour la liaison oxime ont été mises au point conjointement à l'évaluation in vitro et in cellulo des peptides cycliques. Appliquées à la conjugaison avec un peptide de pénétration cellulaire, ces méthodes ont montré que ces inhibiteurs vectorisés présentent un effet anticancéreux prometteur<br>In response to several stresses, p53 protein is activated to promote metabolic changes, cell cycle arrest and DNA repair. In case of strong DNA damages, this protein can also lead to the self-destruction of the cell. This mechanism of programmed cell death, called apoptosis, naturally occurs from the embryonic stage and regulates the cell stock. Nevertheless, this essential role is inactivated in cancer cells where, in half of the cases, p53 is mutated. HDM2 protein causes the degradation of p53 by polyubiquitinylation thus allowing cancer cells to escape this control despite their strong degeneration. Inhibition at different levels of ribosome biogenesis leads to the stabilization and accumulation of p53. This finely regulated process uses nearly 200 assembly factors, including hCINAP. This factor interacts with the ribosomal protein RPS14 during the last stage of maturation of the small ribosomal subunit. RPS14 can also bind HMD2 and release the inhibition of p53. The aim of this thesis remains on the chemical synthesis of peptide inhibitors targeting the hCINAP/RPS14 interaction to restore the activity of p53 and disturb ribosome biogenesis to trigger a dual antitumor effect. This work is based on a crystallographic structure of Fap7, archaeal form of hCINAP, in complex with RPS14. By mimicking the C-terminal loop of RPS14, these innovative cyclic peptides aim to promote RPS14/HDM2 binding. Peptide ligation methods using thiazolidine ring for oxime bond have been developed in conjunction with the in vitro and in cellulo evaluation of cyclic peptides. Vectorized inhibitors derived from this conjugation methods with a cell penetrating peptide exhibited a promising anticancer effect
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Huber-Villaume, Sophie. "Impact des ligands de PPARs, et leurs dérivés, sur les cellules cancéreuses coliques humaines : modifications des statuts redox et glycolytique." Thesis, Université de Lorraine, 2014. http://www.theses.fr/2014LORR0217/document.
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La Pioglitazone appartient à la famille des thiazolidinédiones et le Fénofibrate à la famille des fibrates. Ces molécules sont, respectivement, des agonistes synthétiques du récepteur activable par les proliférateurs de peroxysomes γ (PPARγ) et PPARα, membres de la famille des récepteurs nucléaires aux hormones. Le traitement de cellules cancéreuses humaines par ces molécules limite la croissance et peut induire leur apoptose. Cependant, l’impact de ces traitements sur les cellules cancéreuses est en partie dû à une action indépendante de l’activation du récepteur et met en cause la génération d'un stress oxydant. Au cours de ces travaux, un analogue de la Pioglitazone, la ΔPioglitazone, qui ne permet pas l’activation de PPARγ, a été synthétisé. Les effets de ces molécules ont été testés sur deux lignées cellulaires établies à partir de cancer colique, HT29 et HCT116. Ces traitements limitent la croissance des cellules cancéreuses sans induire de processus apoptotique. La production d’espèces réactives est responsable d’une diminution du contenu en glutathion intracellulaire. Le stress oxydant généré suite au traitement par la Pioglitazone et la ΔPioglitazone induit l’activation de la voie de signalisation antioxydante Nrf2/Keap1 et l’expression de ses gènes-cibles HO-1 et NQO1. En revanche, bien qu’il induise la production d’un stress oxydant, le Fénofibrate n’entraîne aucune activation de cette voie. De plus, ces trois composés sont responsables d’une modification du métabolisme cellulaire en faveur de la glycolyse. Parallèlement, l’impact de dérivés 4-thiazolidinones, analogues des thiazolidinédione, synthétisés au laboratoire, a été testé. L’effet de ces molécules a été évalué sur la survie cellulaire et le statut redox des cellules HT29. Plusieurs composés présentent une activité antiproliférative et sont capables de générer un stress oxydant sans activer la voie Nrf2/Keap1<br>Peroxisome Proliferator-activated Receptors (PPAR) are members of the nuclear receptor family. Pioglitazone and Fenofibrate belong respectively to the thiazolidinedione and fibrate family. Pioglitazone is an agonist of PPARγ isotype whereas Fenofibrate is an agonist of PPARα isotype. Cancer cell exposure to each ligand inhibits cell growth and triggers apoptosis cell death. However, the effects of respective PPAR ligand on cell survival were found to be independent of receptor activation and were associated to redox changes within the cells. In order to discriminate PPAR independent from PPAR dependent activation, an analogue of Pioglitazone, Δ-Pioglitazone was synthesized. The molecule binds to PPARγ without activating it. Two cancer cell lines established from human colon adenocarcinoma, HT29 and HCT116 were tested. Cell exposure to each molecule inhibited cell growth but cells did not undergo apoptosis cell death. Cell treatment induced the production of reactive species and the decrease of intracellular glutathione content. Pioglitazone or [delta]-Pioglitazone-mediated oxidative stress triggered the activation of the Nrf2/Keap1 pathway as assessed by the increases of Nrf2 target genes expression such as HO-1 and NQO1. In contrast, Fenofibrate treatment increased reactive species production but did no activate this pathway. Moreover, cell exposure to Pioglitazone, Δ-Pioglitazone or Fenofibrate modulated cell metabolism, notably by enhancing glycolysis. In parallel, impact of 4-thiazolidinone derivatives synthesized in the laboratory was tested. These molecules are analogues of thiazolidinedione. Effect of 4-thiazolidinone treatments was assessed to cell growth arrest and redox changes within the HT29 cells. Several molecules have anti-proliferative effect and are able to generate oxidative stress without Nrf2/Keap1 pathway activation
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Fernandez, Xavier. "Réativité des thiazolidines, substances aromatisantes et parfumantes." Nice, 2001. http://www.theses.fr/2001NICE5672.
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Récemment identifiées à l'état de traces dans la goyave et le cupuaçu, les thiazolidines sont des intermédiaires clefs dans la biosynthèse des thiazolines et thiazoles, hétérocycles d'un grand intérêt dans le domaine de la chimie des arômes. Ce travail a pour objectif l'étude des thiazolidines et des réactions d'oxydation sélectives sur ces dernières. La première partie de cette étude complète les travaux existants sur les thiazolidines principalement en ce qui concerne la stéréochimie et l'étude de leur réaction d'isomérisation. Pour cela, nous nous sommes principalement appuyés sur la RMN (1D et 2D) et la modélisation moléculaire. Dans un deuxième temps, l'étude des réactions d'oxydation sélective de cet hétérocycle a permis la mise au point de méthodes de synthèse originales, catalysées ou non, conduisant aux D2 et D3-thiazolines. La synthèse des thiazoles, thiazolidine-1-oxydes et thiazolidine-1,1-dioxydes ainsi que l'étude de la stéréochimie de ces composés est également présentée. Une analyse sensorielle d'une partie des produits obtenus révèle des notes intéressantes, le plus souvent de type alimentaire et des seuils de perception de l'ordre du ppm.
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Norisada, Nobuyoshi. "Antidiabetic and adipogenic properties in a newly-synthesized thiazolidine derivative, FPFS-410." Kyoto University, 2007. http://hdl.handle.net/2433/135906.
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Brockmann, Anette [Verfasser]. "GSTP1-1 and thiazolide-induced apoptosis in colon carcinoma cells / Anette Brockmann." Konstanz : Bibliothek der Universität Konstanz, 2015. http://d-nb.info/1088797318/34.
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Martinez, Audrey. "Synthèse et caractérisation de thiazolidines et d'oxazolidines dérivées d'α-aminoacides naturels - intérêt dans une approche de prodrogues de répulsifs naturels". La Réunion, 2009. http://www.theses.fr/2009LARE0004.
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L'exploitation des principes actifs naturels et d'une approche de vectorisation peut contribuer au développement durable et à la chimie verte. La première partie décrit la synthèse, la caractérisation et la stabilité en solution d'oxazolidines et de thiazolidines diversement substituées dérivant de trois α-aminoacides naturels (L-cystéine, L-sérine et L-thréonine) pour évaluer la stratégie basée sur une réaction de cyclocondensation avec des composés carbonylés (aldéhydes et cétones). Une voie de synthèse originale (réaction one pot) qui permet de contourner l'équilibre tautomérique des hétérocycles saturés 1,3-X,N (type I) a été mise au point pour la synthèse d'hétérocycles N-substitués (type II). Les paramètres structuraux pouvant moduler la stabilité des cycles ont été également identifiés. La seconde partie décrit l'exploitation des résultats précédents pour la conversion d’un répulsif olfactif naturel en prodrogues de type oxazolidine et thiazolidine dans le cadre de la prévention primaire des maladies à transmission vectorielle. La mise en place d’une évaluation biologique structurée est également décrite à partir d’une série représentative des formes dérivées du principe actif. Les résultats préliminaires démontrent l'intérêt des prodrogues et ses paramètres structuraux qui contribuent à sa tolérance cellulaire par rapport au principe actif ou au leader de référence (DEET), au contrôle du relargage dans des nanocapsules et à son efficacité pour la protection individuelle contre Aedes albopictus. L'ensemble des résultats conforte l'intérêt de cette approche de prodrogues pour la vectorisation d'autres principes actifs naturels<br>Combination of natural bioactive compounds with a drug delivery approach should contribute to sustainable development and chemistry. The first part describes the synthesis, characterization and stability in solution of structurally diverse oxazolidines and thiazolidines derived from three natural α-amino acids (L-cysteine, L-serine and L-threonine) to assess the potential of the chemical route based on a cyclocondensation reaction of carbonyl compounds (aldehydes and ketones). A convenient protocol (one pot reaction) has been developed when performing the synthesis of highly substituted heterocycles (type II) and proved to be useful to overcome the ring-chain equilibrium of saturated 1,3-X,N-heterocycles (type I). Interestingly, structural parameters which could modulate the ring stability have been identified. Based on the above results, the second part is related to the synthesis of prodrug forms (oxazolidines and thiazolidines) of a natural olfactory repellent for primary prevention of vector-borne diseases. Preliminary bioassays are described for representative prodrugs compared to the parent bioactive compound or a gold standard (DEET). Appropriate structural features of the prodrugs resulted in lower cell toxicity, control of the release process in nanocarriers and higher personal protection time against Aedes albopictus. The overall results ascertain the potential of this prodrug approach for other natural bioactive compounds
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Ferreira, Cavalcanti de Albuquerque Julianna. "Thioxo-imidazolidinones et thiazolidinones substituées : synthèse, structure et étude pharmacologique." Université Joseph Fourier (Grenoble), 1996. http://www.theses.fr/1996GRE18012.
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Bregant, Sarah. "Synthèse de thiazolidines fonctionalisées, incorporation dans des PNA et étude des propriétés d'appariement." Paris 6, 2002. http://www.theses.fr/2002PA066397.
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Önen, Filiz Esra. "Conception, synthèse et évaluation de nouvelles familles de composés anticancéreux et antibactériens." Paris 6, 2007. http://www.theses.fr/2007PA066046.
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L’identification de petites molécules contrôlant les mécanismes d’action des systèmes biologiques est un problème central de la chimie médicinale. Afin d’identifier des structures actives sur la thymidilate synthase X, une cible importante pour le développement d’agents antibactériens spécifiques, nous avons mis au point la synthèse deux nouvelles familles de composés comportant des squelettes triazole et thiazolidine. Les différentes évaluations conduisent à l’identification de deux entités possédant un pouvoir inhibiteur important. Ces deux familles ont également été testées sur des lignées de carcinome hépatocellulaire ainsi qu’une lignée cellulaire du cancer du sein. Le criblage a révélé une structure présentant une grande cytotoxicité.
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Barbry, Didier. "Synthèse et étude structurale de thiazolidines substituées sur les positions 2, 4 ou 5." Lille 1, 1986. http://www.theses.fr/1986LIL10105.
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Synthèse de thiazolidines substituées par un ou plusieurs méthyle et par isopropyles, t-butyle ou phényle et éventuellement un ou plusieurs méthyle ; étude de structure en solution par RMN 1H, 13C, 15N et à l'état solide par diffraction Rx (pour la phényl-2 thiazolidine) ; discussion sur l'effet anomère
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Barbry, Didier. "Synthèse et étude structurale de thiazolidines substituées sur les positions 2, 4 ou 5." Grenoble 2 : ANRT, 1986. http://catalogue.bnf.fr/ark:/12148/cb37595714w.
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Oliveira, Albert Rocha de. "Síntese, caracterização estrutural e avaliação antineoplásica de derivados 5-benzilideno-3-benzil-tiazolidina-2,4-diona." Universidade Federal de Pernambuco, 2015. https://repositorio.ufpe.br/handle/123456789/16872.
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Previous issue date: 2015-02-27<br>CAPEs<br>Câncer é o nome dado a uma grande variedade de doenças que possuem como principal característica um crescimento celular contínuo e desordenado. A quimioterapia é uma das alternativas terapêuticas no combate ao câncer, entretanto as atuais opções terapêuticas são frequentemente acompanhadas de fortes efeitos colaterais. Inúmeros trabalhos vêm sendo desenvolvidos nos últimos anos, relacionando as moléculas tiazolidínicas com atividades antineoplásicas. No presente trabalho, foram realizadas a síntese e a caracterização estrutural de cinco derivados da série 5-benzilideno-3-benzil-tiazolidina-2,4-diona, seguidas da avaliação da citotoxicidade de dois desses compostos sobre células mononucleares do sangue periférico (PBMCs) e sobre as linhagens de células neoplásicas DUO-145, HepG2, K562 e RAJI, utilizando ensaios de MTT. Inicialmente, realizou-se a síntese da tiazolidina-2,4-diona, a partir da reação entre ácido monocloroacético e tiouréia. Em seguida, realizaram-se N-alquilações, em uma solução equimolar de hidróxido de sódio, utilizando a tiazolidina-2,4-diona e diferentes haletos de benzila substituídos, obtendo-se intermediários 3-benzil-tiazolidina-2,4-diona substituídos. Os compostos finais foram sintetizados a partir de reações de condensação na posição 5 do anel tiazolidínico, reagindo-se os intermediários, anteriormente sintetizados, com benzaldeídos, obtendo-se os compostos tiazolidínicos finais, com rendimentos entre 52 e 70%. A estrutura química dos compostos sintetizados foi determinada por espectroscopia de ressonância magnética nuclear de 1H e de 13C, espectroscopia de infravermelho e por espectrometria de massas. A avaliação da seletividade citotóxica dos compostos 5-(3-cloro-benzilideno)-3-(2-cloro-6-flúor-benzil)-tiazolidina-2,4-diona (LPSF/GQ-103) e 5 - (2,4-dimetóxi-benzilideno) - 3 - (2-cloro-6-flúor-benzil)-tiazolidina-2,4-diona (LPSF/GQ-106) foi realizada sobre PBMC’s, através de ensaios MTT, apresentando resultados com viabilidade acima de 90%. Nos ensaios de citotoxicidade tumoral, a linhagem DUO-145 apresentou melhor suceptibilidade aos compostos testados, com valores de IC50 18,18 μM para o LPSF/GQ-103 e IC50 24,13 μM para o LPSF/GQ-106.<br>Cancer is the name given to a variety of diseases that have a major feature a continuous and disorderly cell growth. Chemotherapy is one of therapeutic alternatives to fight cancer, but the current therapeutic options are often accompanied by severe side effects. Numerous studies have been developed in recent years talking about the thiazolidine molecules with antineoplastic activities. In this study, we realized the synthesis and structural characterization of five derivatives of the series 5-benzylidene-3-benzyl-thiazolidine-2,4-dione, followed by evaluation of cytotoxicity of two such compounds on peripheral blood mononuclear cell (PBMCs) and on the tumor cell lines DUO-145, HepG2, K562 and RAJI, using MTT assays. Initially we realized the synthesis of thiazolidine-2,4-dione, from the reaction between monochloroacetic acid and thiourea. Then, it were realized N-alkylations using thiazolidine-2,4-dione and various substituted benzyl halides obtaining the intermediates 3-benzyl-thiazolidine-2,4-dione substituted. The final compounds were synthesized from condensation reaction in position 5 of the thiazolidine ring, by reacting intermediates previously synthesized with benzaldehydes obtaining tiazolidínicos final compounds in yields between 52 and 70%. The chemical structure of the synthesized compounds was determined by 1H and 13C nuclear magnetic resonance spectroscopy, by infrared spectroscopy and by mass spectrometry. The evaluation of selective cytotoxicity of the compounds 5-(3-chloro-benzylidene)-3-(2-chloro-6-fluoro-benzyl)-thiazolidine-2,4-dione (LPSF/GQ-103) and 5-(2,4-dimethoxy-benzylidene)-3-(2-chloro-6-fluoro-benzyl)-thiazolidine-2,4-dione (LPSF/GQ-106) was performed on PBMC’s by MTT assay, presenting results viability above 90%. In the tumor cytotoxicity assays, the tumor cell line DUO-145 had better cytotoxic susceptibility to the tested compounds, with 18.18 μM IC50 value for the compound LPSF/GQ-103 and 24.13 μM IC50 value for the LPSF/GQ-106.
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ALMEIDA, Marcel Lucas de. "Síntese, caracterização e atividade biológica de novos derivados e atividade biológica de novos derivados da 3-(acridina-9-imetil) tiazolidina-2,4-diona." Universidade Federal de Pernambuco, 2015. https://repositorio.ufpe.br/handle/123456789/16873.
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Previous issue date: 2015-02-19<br>CAPEs<br>Estima-se que até 2030 o câncer será responsável por até 12 milhões de óbitos. Tendo em vista a necessidade de novos tratamentos para o câncer, este trabalho tem como objetivo sintetizar, caracterizar estruturalmente e avaliar a atividade anticâncer de sete novos derivados tiazacridínicos (LPSF AA-56, LPSF AA-57, LPSF AA-59, LPSF AA-60, LPSF AA-61, LPSF AA-62, LPSF AA-63). Estes derivados provém da hibridização molecular dos núcleos de tiazolidina e de acridina. As sínteses para obtenção destes compostos foram otimizadas para obtenção de um melhor rendimento. A síntese da tiazolidina-2,4-diona (TZD) foi feita por reação de ciclização. Uma posterior N-alquilação da TZD em presença de uma base e da 9-(bromo-metil)acridina, conduziu a formação do intermediário LPSF AA-1A. Os intermediários ésteres de Cope (IPs) foram obtidos a partir de uma reação de condensação Knoevenagel. A última etapa ocorreu por uma reação de adição de Michael através de reação entre a TZD N-alquilada com os ésteres de Cope, formando os derivados tiazacridínicos substituídos. A pureza e comprovação estrutural das moléculas sintetizadas foram obtidas através de cromatografia líquida acoplada a espectrômetro de massa (LC-MS), infravermelho (IV) e ressonância magnética nuclear (RMN) de hidrogênio. Ensaios de citotoxicidade dos derivados sintetizados foram realizados em células leucêmicas, fígado e próstata. Entre os compostos sintetizados, o LPSF AA-57 exibiu a atividade anti-cancerígena mais potente contra as linhagens celulares Jurkat (6,63 ± 2,65 μM), HL-60 (6,51 μM), K562 (3,97 ± 1,36 μM) e o LPSF AA-60 exibiu a atividade anti-cancerígena mais potente contra DU 145 (7,22 ± 3,12 μM).<br>It is estimated that cancer will be responsible for up to 12 million deaths by 2030. Given the need for new treatments for cancer this work aims to synthesize, characterize structurally and evaluate the anti-cancer activity of seven new thiazacridines derivatives (LPSF AA-56, LPSF AA-57, LPSF AA-59, LPSF AA-60, LPSF AA-61, LPSF AA-62, and LPSF AA-63). These derivatives derived of molecular hybridization from nucleus of thiazolidine and acridine. The syntheses for obtaining these compounds were optimized to obtain the best performance. Synthesis of thiazolidine-2,4-dione (TZD) was carried out by cyclization reaction. A further N-alkylation of the TZD in the presence of a base and 9-(bromomethyl)acridine, leading to formation of intermediate LPSF AA-1A. Intermediate esters of Cope (IPs) were obtained from a Knoevenagel condensation reaction. The last step was by a Michael addition, reaction between the N-alkylated TZD with ester of Cope, forming substituted thiazacridines derivatives. The purity and structural confirmation of the synthesized molecules were obtained from liquid chromatography coupled to mass spectrometry (LC-MS), infrared (IR) and Proton nuclear magnetic resonance (NMR). Assays of cytotoxicity of the synthesized products was conducted in leukemic cells, liver and prostate. Among the synthesized compounds, the LPSF AA-57 exhibited the most potent anti-cancer activity against cell lines Jurkat (6,63 ± 2,65 μM), HL-60 (6,51 μM), K562 (3,97 ± 1,36 μM) and the LPSF AA-60 exhibited the most potent anti-cancer activity against DU 145 (7,22 ± 3,12 μM).
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Li, Kaicheng. "Exploration and Applications of Boron Mediated Bioconjugation Chemistries:." Thesis, Boston College, 2020. http://hdl.handle.net/2345/bc-ir:108953.
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Thesis advisor: Jianmin Gao<br>Besides their broad applications in organic chemistry, boronic acids are also increasingly seen in a variety of biological applications. For instance, they have been used in therapeutic drugs for chemotherapy or probes for the detection of saccharides. One unique feature of boronic acids is that they are capable of forming reversible complexes with sugars or even amino acids. Importantly, they are known to have low inherent toxicity to human. In this work, we have focused on two important reactions involving boronic acids: boronate ester formation, in which boronic acids react with diols and iminoboronate formation in which boronic acids form dative bonds with neighboring amino groups. We have demonstrated the potential of these reactions in bacteria targeting or protein modification. We envisioned that boronic acids could be used as a great warhead to be included in the development of novel antibiotics to counter antibiotic resistance of bacteria, which has emerged to be a serious clinical problem. Different from conventional antibiotics, we decided to utilize reversible covalent chemistries in the design of bacterium binding probes. Inspired by the diol-rich environment on bacterial surface, the first strategy took advantage of the reaction between boronic acid and diols to form boronate esters. We have rationally designed a linear peptide containing five copies of the ‘Wulff-type’ boronic acids or bicyclic amphiphilic peptides with two copies of boronic acids. We examined their capability of binding to E. coli cells or their bactericidal activity against S. aureus. Furthermore, we established a synthetic peptide library (OBTC) incorporating the 2-acetylphenyl boronic acid (2-APBA) warhead to form iminoboronate with the target-lipid II, a precursor for the biosynthesis of peptidoglycan. Although this library failed to generate any potent peptide hits, it provided useful information regarding the development of a synthetic library as well as the screening process. As an extension of the iminoboronate chemistry, thiazolidinoboronate (TzB) attracted our attention for its unique reaction mechanism, superior kinetics and excellent selectivity towards N-terminal cysteine residues. In this work, we have proposed an additional acyl transfer following TzB formation to turn this reaction into an irreversible conjugation. The new reaction inherits the fast kinetics and outstanding selectivity from the TzB chemistry. Excitingly, the product of TzB mediated acyl transfer survived complex conditions such as SDS-PAGE and LC/MS. This reaction was also applied to modify two recombinant proteins with N-terminal cysteine residues or to create a C5C phage library with two distinct modifications. We have further extended the substrate from cysteine to diaminopropionic acid (Dap), serine and tris base. We were delighted to observe imidazolidino boronate (IzB) formation and oxazolidino boronate (OzB) formation, which led to the design of cysteineresponsive probes or peptides that can be spontaneously cyclized in neutral aqueous conditions<br>Thesis (PhD) — Boston College, 2020<br>Submitted to: Boston College. Graduate School of Arts and Sciences<br>Discipline: Chemistry
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Ericson, Mark David. "A novel iterative reducible ligation strategy for the synthesis of homogeneous gene delivery polypeptides." Diss., University of Iowa, 2012. https://ir.uiowa.edu/etd/3449.
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The ability to safely delivery efficacious amounts of nucleic acids to cells and tissues remains an important goal for the gene therapy field. Viruses are very efficient at delivering DNA, but safety concerns limit their clinical use. Nonviral vectors are not as efficient at DNA delivery, but have a better safety profile. Limiting the efficaciousness of nonviral vectors are the numerous extra and intracellular barriers that must be overcome for successful DNA delivery in vivo. While single polymers can successfully transfect immortalized cell lines in vitro, multicomponent gene delivery systems are required for delivery in vivo. Key in the development of multicomponent systems is their syntheses. Optimization of a nonviral gene delivery system requires the development of methodologies that incorporate the different components in a controlled fashion, generating homogeneous gene delivery vectors. Such syntheses ensure every polymer has the different components required for successful delivery. The amount of each component and location within the gene delivery system can also be varied systemically, allowing optimization of the vector.
The overall scope of this thesis is to develop a chemical method to iteratively couple gene delivery peptides through reducible disulfide bonds. The synthesis of such polypeptides allows the triggered disassembly of a polypeptide polyplexed with DNA upon cellular uptake. To synthesize homogeneous gene delivery polypeptides, a novel iterative reducible ligation strategy was developed, based upon the use of a thiazolidine masked cysteine. Initial studies demonstrated that a thiazolidine could be unmasked to a cysteine in the presence of a disulfide bond without side reaction, though the reported thiazolidine hydrolysis conditions of aqueous methoxyamine were insufficiently robust for high yielding ligations. Discovery of a novel silver trifluoromethanesulfonate hydrolysis led to an efficient process for generating reducible polypeptides, as evidenced in the synthesis of a 4 component polypeptide.
Due to the success of the thiazolidine mediated iterative ligation strategy, cysteines were replaced by penicillamines to produce more stable disulfide bonds. The mild thiazolidine hydrolysis and subsequent peptide conjugation reactions led to attempt the iterative ligation strategy on a solid support, eliminating purification steps that lowered the yields in the solution phase methodology. Initial progress at generating gene delivery peptides that could be incorporated into the synthetic strategy included the generation of a tri-orthogonal cysteine protecting scheme that allowed a third cysteine to be derivatized with a targeting ligand or stealthing polymer. Due to the use of terminal cysteines in the iterative ligation strategy, a PEG stealthing polymer could be placed in the center of a polyacridine gene delivery peptide with only a small decrease in the ability to condense and protect DNA during systemic circulation. A convergent synthesis was also developed that was able to synthesize large polypeptides in fewer linear steps. The synthetic methodology of thiazolidine mediated iterative reducible ligation developed in this thesis is important in the gene therapy field as it allows the construction of polypeptides that can be systemically optimized, potentially resulting in highly efficacious nonviral gene delivery.
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Law, Ho. "Synthèse et étude conformationnelle d'hétérocycles soufrés radioprotecteurs : mécanisme réactionnel de formation du cycle thiazolidine : obtention de pyrrole N-éthanethiols." Université Joseph Fourier (Grenoble), 1992. http://www.theses.fr/1992GRE18003.
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Quaile, Andrew Thomas. "Nitazoxanide and the Thiazolides : Investigation into Drug Meditated Cellular Responses and Identification of Novel Drug Interactors." Thesis, University of Liverpool, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.526916.
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CAVALCANTE, SILVA JACQUELINE. "Effects of a new thiazolidine compound (GQ-11) on tissue repair process in models of insulin resistance and ischemia/reperfusion." Doctoral thesis, Università degli studi di Genova, 2019. http://hdl.handle.net/11567/982439.
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The thiazolidinediones (TZDs) class comprises drugs with hypoglycemic effects, reducing insulin resistance in peripheral tissues. Our group has demonstrated in preliminary in vivo data that a new TZD, GQ-11, improves insulin resistance as well as modulates cytokines involved in inflammatory process, suggesting an interesting approach for therapeutic alternatives in tissue repair, especially in metabolic decompensation cases, as insulin resistance and ischemia-reperfusion. In this context, the aim of this study was to investigate GQ-11 effects in tissue repair in three different models: insulin resistance in db/db mice, reconstructed human epidermis (RHE) in glycated collagen matrix and ischemia/reperfusion in Wistar rats.
In insulin resistance context, GQ-11 treatment showed to upregulate expression of anti-inflammatory mediators, such as IL-10, TGF- and Arg-1, besides downregulating expression of pro-inflammatory cytokines both in db/db mice wounds and in macrophages, besides increasing re-epithelization and collagen deposition. In addition, the treatment also induced keratinocytes proliferation and fibroblasts differentiation in RHE.
In ischemia-reperfusion model, same anti-inflammatory effect was observed along anti-oxidant properties through regulation of enzymes, such as catalase, GPx and TBARS formation decrease, besides 18F-FDG uptake decrease in Positron Emission Tomography (PET) imaging, suggesting decrease of inflammation process related to reperfusion after aorta clamping.
Concluding, the treatment with a dual PPAR/ agonism, such as GQ-11, promotes a central anti-inflammatory effect, suggesting a new approach to tissue repair management in diabetes and in prevention of ischemia-reperfusion syndrome post-surgery.
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Amato, Douglas Vincent. "LATENT CYSTEINE RESIDUES FROM POLYMERS PREPARED VIA FREE AND CONTROLLED RADICAL POLYMERIZATIONS." DigitalCommons@CalPoly, 2013. https://digitalcommons.calpoly.edu/theses/972.
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One less commonly used “click” reaction is thiazolidine chemistry. Thiazolidine chemistry is a commonly used reaction used in biological systems because the reaction requires the presence of both cysteine (a common amino acid) and an aldehyde or ketone. If cysteine residues could be incorporated into a polymer then a variety of applications could be developed. Polymers containing free thiols (aka thiomers) have developed in the last decade to become great mucoadhesives. If there was a facile route to control the amount of free thiols along the polymer then more fine-tuned and potentially stronger adhesives could be made. For these reasons the attachment of cysteine residues in a facile way via reversible addition fragmentation chain transfer (RAFT) polymerization or small molecule synthesis was researched. The incorporation of latent cysteine residues into the polymer via post polymerization modification proved to be less successful. However protected cysteine molecules have been successfully ligated onto polymerizable monomers and have been show to be easily deprotected in the presence of an acid source.
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Myllymäki, V. (Vesa). "Design, synthesis and testing of new chiral sulfide catalysts for Corey-Chaykovsky reaction." Doctoral thesis, University of Oulu, 2001. http://urn.fi/urn:isbn:9514265718.
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Abstract
The first part of this monograph discusses the asymmetric, ylide based, reagent
controlled epoxidations. Both different chiral ylides and epoxidation processes,
stoichiometric and catalytic, are reviewed.
In the following part, new chiral sulfide catalysts were discovered as enantioselective
catalysts for the Corey-Chaykovsky reaction (epoxidation of aldehydes via sulfonium
ylides). Using a crystal structure of an oxazolidine derivative as a starting point, a
thiazolidine ligand family was designed, synthesized and finally employed as catalysts in
the asymmetric epoxidation of benzaldehyde. The ligands were prepared starting from
L-valine, L-tert-leucine, D-penicillamine and L-cysteine. The
differently tuned thiazolidine ligands were demonstrated to catalyze the formation of
trans-stilbene oxide with varying enantioselectivities. On the basis
of these results, a mechanistic rationale for the asymmetric induction was presented. The
results heavily demonstrated the importance of ring rigidity as an affecting factor in
the enantioselectivity of the tested thiazolidines.
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ANDRADE, Fabrício Havy Dantas de. "Estudos de caracterização de um novo agente esquistossomicida e tripanossomicida (LPSF/GQ-238)." Universidade Federal de Pernambuco, 2016. https://repositorio.ufpe.br/handle/123456789/18628.
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Previous issue date: 2016-02-16<br>FACEPE<br>CAPES<br>O 3-(2,6-diflúor-benzil)-5-(5-bromo-1H-indol-3-ilmetileno)-tiazolidina-2,4-diona
(LPSF/GQ-238) é um análogo indólico-tiazolidínico, apresenta potencial atividade
esquistossomicida e tripanossomicida. Poucos relatos na literatura mostram a
eficácia de uma substância contra a esquistossomose e a doença de chagas. Estas
doenças são consideradas doenças debilitantes e afeta milhões de pessoas no
mundo. Assim, o objetivo deste trabalho foi realizar a caracterização físico-química
do LPSF/GQ-238 visando conhecer suas propriedades químicas e físicas para
desenvolvimento de uma nova alternativa de tratamento para as doenças
supracitadas. O estudo abrangeu a caracterização físico-química, estabilidade
térmica e compatibilidade fármaco-excipiente por técnicas espectroscópicas (IV,
RMN), termoanalíticas (DSC, DSC-fotovisual, TG e Pyr-CG/EM), validação do
método analítico, bem como DRX e MEV. Os resultados obtidos da avaliação físicoquímica
do LPSF/GQ-238 frente a diferentes técnicas permitiram caracterizá-lo do
ponto de vista físico, químico e morfológico. O protótipo apresentou-se com 99,5%
de pureza, funde a 272,48 ± 0,28 °C e entalpia de 78,31 ± 4,31 J.g-1 com pico
endotérmico de fusão característico de uma forma cristalina que foi corroborado pela
DRX, com habito cristalino do tipo agulha por MEV, apresenta baixa solubilidade
aquosa e cinética de decomposição de ordem zero. O estudo de compatibilidade
evidenciou possíveis incompatibilidades químicas e/ou físicas entre o LPSF/GQ-238
e os excipientes estudados. Concluí-se que a caracterização da NEQ obteve
resultados sólidos sobre o comportamento físico e químicos de um protótipo
antiparasitário para tratar a esquistossomose e a doença de chagas.<br>The 3-(2,6-difluoro-benzyl)-5-(5-bromo-1H-indol-3-ylmethylene)thiazolidine-2,4-dione
(LPSF/GQ-238) is an indole-thiazolidine analogue with schistosomicidal and
trypanocidal potential activity. Few reports in the literature show the effectiveness of
a substance against schistosomiasis and Chagas disease simultaneously. These are
considered debilitating diseases affecting millions of people worldwide. The objective
of this study was to perform the physicochemical characterization of LPSF/QA-238
aiming to know their chemical and physical properties for the development of a new
alternative treatment for the above diseases. The study covered the physicochemical
characterization, thermal stability, and drug-excipient compatibility by spectroscopic
techniques (IR, NMR), thermoanalytical (DSC, DSC-fotovisual, TG and Pyr-GC/MS),
validation of analytical method, as also, XRD and SEM .The results of
physicochemical evaluation of LPSF/QA-238 compared to different techniques
allowed characterize it physical, chemical and morphologically. The prototype
presented 99.5% purity, melting at 272.48 ± 0.28 °C and enthalpy of 78.31 ± 4.31 Jg1
, endothermic peak of melting characteristic of a crystalline form which was
confirmed by XRD, with crystalline habit needle type observed in the SEM, has low
aqueous solubility and kinetics of order decomposition zero.The compatibility study
highlighted possible chemical and / or physical incompatibilities between LPSF / QA238
and the excipients studied.It is concluded that the new chemical entity
characterization obtained actual results about the physical and chemical behavior of
a prototype antiparasitic to treat schistosomiasis and Chagas disease.
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Maurer, Frauke [Verfasser], and Uli [Akademischer Betreuer] Kazmaier. "Anwendungen von Oxazolin- und Thiazolin-Liganden in der Asymmetrischen Katalyse / Frauke Maurer. Betreuer: Uli Kazmaier." Saarbrücken : Saarländische Universitäts- und Landesbibliothek, 2011. http://d-nb.info/1051326095/34.
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Ripani, Paola [Verfasser]. "Synergy between thiazolides and glutathione-S-transferases in cell death induction in colorectal tumor cells / Paola Ripani." Konstanz : KOPS Universität Konstanz, 2019. http://d-nb.info/1204829527/34.
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Miranda, Guarda Vera Lucia de. "1,4-benzothiazinones et thiazolidinones substituées : synthèse, étude stucturale et activité antibactérienne." Université Joseph Fourier (Grenoble), 1998. http://www.theses.fr/1998GRE18004.
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Gnudi, F. "IMMUNOMODULATORY EFFECTS OF NITAZOXANIDE AND RELATED MOLECULES." Doctoral thesis, Università degli Studi di Milano, 2014. http://hdl.handle.net/2434/231146.
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Background: Nitazoxanide (Alinia®, NTZ) and its active circulating metabolite tizoxanide (TIZ) belong to a new class of anti-infective agents active against parasites, anaerobic bacteria, and viruses. Nowadays, NTZ is licensed in the United States for the treatment of diarrhea caused by Cryptosporidium parvum and Giardia lamblia in adults and children older than twelve months of age. The amplitude of the spectrum of pathogens targeted by NTZ and new-generation non-nitro thiazolides, makes it very unlikely that the action of these compounds is mediated by a pathogen-specific mechanism(s), suggesting instead that thiazolides act as immunomodulants. To date, the potential effect of these compounds on immune responses has nevertheless not been analysed. In particular, because innate immunity and type 1 interferons are pivotal in early and effective antiviral immune responses that are not antigen-restricted, it is plausible to hypothesize that thiazolides could potentiate this arm of the immune system. To verify this possibility, we performed extensive in vitro analyses on the immunomodulatory effects of TIZ and the second generation non-nitro thiazolide RM4848 using two different models of viral infection: Influenza and HIV-1.
Methods: Peripheral blood mononuclear cells (PBMCs) from 20 healthy donors were stimulated with influenza virus antigen (FLU) or infected with HIV-1BaL strain and cultured in presence/absence of TIZ or RM4848. Thiazolide effects on innate immunity were examined by evaluating TLRs expression on monocytes, IFN-secretion by dendritic cells, cytokine and chemokine production, mRNA expression of multiple genes involved in TLR, type I IFN and in cholesterol metabolism pathways.
Results: Thiazolides are associated with strong immunomodulatory effects. Notably, these compounds, both in FLU-stimulated and in HIV-1-infected cells, significantly increase: 1) TLR-expression on monocytes, 2) IFN production, 3) chemokine and cytokine production, 4) mRNA expression of different genes operating in the TLR and type I IFN pathways, 5) genes involved in cholesterol metabolism and efflux.
Conclusions: Data herein show that thiazolides are potent type I IFN inducers, triggering a selective activation of several IFN-stimulated gene (ISG) pathway.
Thus, increased expression of innate antiviral factors and the different modulation of genes involved in cholesterol metabolism and efflux suggest a new mechanism of action mediated by thiazolides.
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Faury, Philippe. "Perspectives chimiothérapeutiques des maladies associées aux rétrovirus : concept, modélisation, synthèse et évaluation biologique d'analogues nucléosidiques non classiques (thiazolidines, oxathiolanes et tétrazoles)." Aix-Marseille 2, 1995. http://www.theses.fr/1995AIX22050.
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Actuellement lorsqu'un patient entre dans la phase active des maladies associees a l'infection par le virus de l'immunodeficience humaine (vih), le traitement clinique qu'il recoit, est base sur l'association ou combinaison de drogues appartenant a la classe des analogues nucleosidiques qui inhibent une enzyme-cle du cycle de replication virale: la transcriptase inverse. Concevoir et realiser la synthese chimique de nouvelles molecules complementaires represente l'objectif majeur des travaux presentes dans ce memoire. Le premier chapitre, concernant les relations entre la structure et l'activite inhibitrice des analogues nucleosidiques, souligne l'importance des heteronucleosides qui incorporent un ou plusieurs heteroatomes dans le cycle ribosyle. De plus, avec l'aide du modele predictif de l'activite anti-vih base sur la modelisation moleculaire qui est propose, les structures de nouveaux analogues nucleosidiques ont pu etre conceptualisees. La synthese d'heterocycles oxathiolanes et thiazolidines 2,5-disubstitues servant de pseudoriboses et la fonctionnalisation des cycles thiazolidines en position 5 par benzoylhydroxylation et par la reaction de pummerer font l'objet du second chapitre. L'importance de la nature du groupement protecteur de l'azote endocyclique lors de la synthese est egalement soulignee. La synthese des analogues nucleosidiques sur la base des heterocycles obtenus et l'etude des reactions de couplage et des activites biologiques sont decrites dans le troisieme chapitre. Aucune activite anti-vih significative n'a ete observee pour les composes synthetises, cependant ces resultats confirmes a posteriori par modelisation moleculaire, ont permis de definir de nouveaux heteronucleosides modeles
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Silva, Júnior Edeildo Ferreira da. "Planejamento de potenciais inibidores de enzimas do parasito Trypanosoma cruzi: síntese, docking e avaliação biológica." Universidade Federal de Alagoas, 2015. http://www.repositorio.ufal.br/handle/riufal/1511.
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Neglected diseases constitute a major public health problem worldwide, quantifying a total of 1 billion people suffering from some kind of infection of bacterial, viral or parasitic origin. Among them, we can highlight Chagas disease, caused by the parasite Trypanosoma cruzi, which affects more than 8 million people around the world. In order to discover new active compounds against T. cruzi, developed herein the synthesis of new prototypes of thiophene-2- thioureic and 2-iminothiazolidine rationally designed with potential antichagasic activity, biological evaluation and study docking. Initially, the start material was the polysubstituted thiophene derivatives synthesized via Gewald reaction, which were converted into thioureic derivatives and then cyclized with five different electrophiles, generating thiophene-2- iminothiazolidine derivatives. The intermediates and final compounds were synthesized in yields between 40 and 98%, and characterized by NMR. For docking study was initially performed by minimizing the energy of the ligands by ArgusLab® software, using AM1, and applying the software AutoDock Tools® and AutoDock Vina®, using the Gasteiger method. All compounds were evaluated in the anti-T. cruzi assays, in vitro, and the most active serie was selected for the cytotoxicity assay (MTT) in J774 cell line. It was possible to determine the enzymes involved in the probable mechanisms of action for the ligands. It has been observed that in 50% of cases, TcDHFR enzyme is the main target of the new compounds, in amastigotes. The pharmacological tests in amastigotes and trypomastigotes, line of C2C12 and MK2 cells was established as validation for the theoretical studies. The compound 3d probably develops its mechanism of action by inhibition of the enzyme TcTS (IC50= 10.3 µM) in trypomastigotes of the parasite. Since the compound 7c possibly acts by inhibition of the enzyme TcDHFR (IC50= 9.2 µM) in amastigotes. In additional, it was proposed that the compound 7b carries out its activity by inhibition of the enzyme TcDHFR (IC50 = 5.0 µM). Finally, it was observed that the most active compounds obtained in this study were more effective than the benznidazole, gold standard drug used in pharmacotherapy clinical of the Chagas disease, additionally has a low cytotoxicity (CC50> 100 µM).<br>As doenças negligenciadas configuram um grande problema de saúde pública mundial, quantificando um total de 1 bilhão de pessoas acometidas por algum tipo de infecção de origem bacteriana, viral ou parasitária. Dentre elas, podemos destacar a Doença de Chagas, causada pelo parasito Trypanosoma cruzi, a qual acomete mais de 8 milhões de pessoas em todo o mundo. No intuito de se descobrir novos compostos ativos capazes de combater o T. cruzi de maneira eficaz, desenvolvemos neste trabalho a síntese de novos protótipos de fármacos tiofeno-2-tioureicos e 2-iminotiazolidínicos racionalmente planejados com potencial atividade antichagásica, avaliação biológica e estudo de docking. Para a síntese dos compostos planejados, partiu-se de derivados tiofenos polissubstituídos, sintetizados via reação de Gewald, os quais foram convertidos em derivados tioureicos e, em seguida, ciclizados com cinco diferentes di-eletrófilos, gerando derivados tiofeno-2- iminotiazolidínicos. Os intermediários e compostos finais foram sintetizados com rendimentos entre 40 e 98%, e caracterizados por RMN. Para o estudo de docking, inicialmente foi realizada a minimização das energias dos ligantes pelo software ArgusLab®, usando o método AM1, e aplicando os softwares AutoDock Tools® e AutoDock Vina®, empregando o método de Gasteiger. Todos os compostos foram submetidos à avaliação in vitro de suas atividades anti-T. cruzi, e a série mais ativa foi selecionada para ensaio de citotoxicidade (MTT) em células da linhagem J774. Foi possível determinar as enzimas envolvidas nos prováveis mecanismos de ação para os ligantes. Foi observado que, em 50% dos casos, a enzima TcDHFR é o principal alvo dos novos composto, em formas amastigotas. Os ensaios farmacológicos em formas amastigotas e tripomastigotas, linhagem de células C2C12 e MK2 funcionaram como métodos de validação dos estudos teóricos. O composto 3d, provavelmente desenvolve seu mecanismo de ação através da inibição da enzima TcTS (IC50= 10.3 µM), em formas tripomastigotas do parasito. Já o composto 7c,possivelmente atua por meio da inibição da enzima TcDHFR (IC50= 9.2 µM) em formas amastigotas. Em adicional, foi proposto que o composto 7b desenvolve sua atividade através da inibição da enzima TcDHFR (IC50= 5.0 µM). Por fim, foi verificado que os compostos mais ativos obtidos neste trabalho se mostraram mais eficientes do que o fármaco benznidazol, padrão-ouro utilizado na clínica farmacológica da doença de Chagas, além destes apresentarem baixa citotoxicidade (CC50> 100 µM).
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Pereira, Elaine. "Adição de enolatos de titanio derivados de N-acil-(4S)-4-isopropil-1,3-tiazolidin-2-tiona a ions N-aciliminios ciclicos : sintese assimetrica dos alcaloides (+)-isoretronecanol e (+)-5-epi-tashiromina." [s.n.], 2005. http://repositorio.unicamp.br/jspui/handle/REPOSIP/249250.
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Orientador: Ronaldo Aloise Pilli<br>Dissertação (mestrado) - Universidade Estadual de Campinas, Instituto de Quimica<br>Made available in DSpace on 2018-08-04T15:31:59Z (GMT). No. of bitstreams: 1
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Previous issue date: 2005<br>Mestrado<br>Quimica Organica<br>Mestre em Química
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Novo, Fernández Olalla. "New contributions to the preparation of compounds derived from L-cysteine with biological activity." Doctoral thesis, Universitat de Lleida, 2017. http://hdl.handle.net/10803/440527.
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Una gran varietat de productes naturals i fàrmacs que inclouen sofre en les seves estructures presenten diverses activitats biològiques i aplicacions. Un exemple és la L-cisteïna, un aminoàcid essencial necessari en processos bioquímics dels éssers vius. D’una banda, aquest treball es centra en l’obtenció de tiazolidines a partir de la L-cisteïna amb un grau de qualitat alimentària. La metodologia es basa en un procés de síntesi en continu i en un sistema d’assecatge d’atomització. A més, es va realitzar un estudi per investigar el rol de la tiazolidina derivada de la D-ribosa com a agent quimioprotector i modulador de glutatió en un model AOM/DSS de carcinogènesi en ratolins. Addicionalment, es van modificar les tiazolidines per tal d'augmentar les seves propietats lipòfiles en vista al seu ús com additius alimentaris en una àmplia varietat de matrius d'aliments. D’altra banda, es van sintetitzar compostos tipus capsaicinoid que incorporaven L-cisteïna i anàlogs en la seva estructura i es avaluar la seva activitat en el receptor TRPV1, que exerceix un paper important com a nexe en la transmissió del dolor. La síntesi, la relació estructura-activitat i els resultats biològics es descriuen en aquest document.<br>Una gran variedad de productos naturales y fármacos que incluyen azufre en sus estructuras presentan diversas actividades biológicas y aplicaciones. Un ejemplo es la L-cisteína, un aminoácido esencial requerido en ciertos procesos bioquímicos de los seres vivo. De una banda, este trabajo se centra en la obtención de tiazolidinas a partir de L-cisteína con grado de calidad alimentaria. La metodología se basa en un proceso de síntesis en continuo y en un sistema de secado por polvorización. También se realizó un estudio para investigar el efecto de la tiazolidina derivada de la D-ribosa como agente quimioprotector y modulador del glutatión en un modelo AOM/DSS de carcinogénesis en ratones i. Adicionalmente, se modificaron las tiazolidines para aumentar sus propiedades lipófilas con objectivo de su uso com aditivos alimentarios en una amplia variedad de matrices alimentarias. Por otra parte, se sintetizaron compuestos tipo capsaicinoide que incorporavan L-cisteína y análogos en su estructura y se evaluó su actividad en el receptor TRPV1, que ejerce un papel importante como a nexo en la transmisión del dolor. La síntesis, la relación estructura-actividad y los resultados biológicos se describen en este documento.<br>A wide variety of sulphur-containing compounds that exist in natural products and drugs present different biological activities and applications. One example is the L-cysteine, an amino acid required for essential biochemical processes in living organisms. On the one hand, this work focuses on the production of thiazolidine-4(R)-carboxylates derived from L-cysteine with food grade quality. The methodology was based on combining a continuous flow reaction and a spray-drying system. Additionally, an study was performed to investigate the role of thiazolidine derived from D-ribose as chemoprotector agent and modulator of glutathione status in a mouse model of AOM/DSS-induced carcinogenesis. Moreover, the highly soluble thiazolidines-4(R)-carboxylic acid derivatives were modified to increase their lipophilicity wih interests to use these thiazolidine derivatives as food ingredients in a wide variety of food matrices. On the other hand, it has been synthesized new capsaicinoid-like compounds incorporating L-cysteine and analogues and it was evaluated their activity on TRPV1, which plays an important role as a nexus in pain transmission. Their synthesis, the structure-activity relationships and biological results are presented.
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Odhar, Hasanain. "Identification of novel scaffolds for Monoamine oxidase B inhibitors." Kent State University / OhioLINK, 2014. http://rave.ohiolink.edu/etdc/view?acc_num=kent1394416913.
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Laduranty, Joëlle. "Mise au point de la préparation de molécules polyfonctionnelles comportant l'unité structurale SCCN de la cystéamine : applications en radioprotection et synthèse organique." Poitiers, 1988. http://www.theses.fr/1988POIT2013.
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Danton, Fanny. "Élaboration de N,S-acétals cycliques et leur transposition en 1,4-thiazines selon des processus en cascade : Nouveaux inhibiteurs de la farnésyltransférase." Thesis, Normandie, 2019. http://www.theses.fr/2019NORMLH31.
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La chimie des hétérocycles est un élément central des sciences chimiques qui contribue fortement à la conception de médicaments ainsi qu’à de nouveaux matériaux de propriétés inédites. Si les hétérocycles azotés de sources naturelles et synthétiques sont les plus largement représentés, les composés aza-soufrés restent relativement peu explorés et par conséquent, ils constituent encore une source d’innovation pour l’exploration d’un nouvel espace chimique.Ce projet de thèse est focalisé en particulier sur les thiazolidines fusionnées ou non porteuses généralement d’un substituant en position acétalique. L’objectif principal de ce projet est de mieux appréhender la réactivité de ces systèmes N,S-acétaliques cycliques peu étudiés de nos jours comparativement aux hétéroanalogues N,O- et encore N,N-acétaliques. Au cours de cette étude, nous avons pu déterminer de nouvelles conditions optimales de la transposition de Morin de ces N,S-acétals en 1,4-thiazines correspondantes. Elles se déclinent en deux étapes via des sulfoxydes ou directement à partir des sulfures congénères par un processus en cascade original utilisant plusieurs agents d’oxydation. Par la suite, la diversification de ces systèmes par couplage CSP2-CSP2 et par C-H fonctionnalisation directe a permis d’accéder à plusieurs nouvelles familles de produits dont les propriétés inhibitrices de la farnésyltransférase sont tout particulièrement prometteuses<br>Heterocyclic chemistry is a central element of the chemical sciences that contribute strongly to drug design as well as to new materials with novel properties. While aza-heterocycles from natural and synthetic sources are the most widely represented, aza-sulphur compounds remain relatively unexplored and therefore are still a source of innovation for the exploration of a new chemical space.This thesis project is focused in particular on thiazolidines fused or not, generally carrying a substituent in acetalic position. The main goal of this project is to better understand the reactivity of these cyclic N,S-acetal systems scarcely studied compared to their hetero- analogues N,O- and N,N-acetals.During this study, we were able to determine new optimal conditions for Morin transposition of these N,S-acetals into corresponding 1,4-thiazines. They proceeded in two steps via sulfoxides or directly from their sulphides congeners by an original cascade process using several oxidizing agents. The subsequent diversification of these systems by CSP2-CSP2 coupling and by direct C-H functionalization has provided access to several new families of compounds with particularly promising inhibitory properties of the farnesyltransferase
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Dušková, Anna. "Syntéza derivátů thiazolidin-2,4-dionu jako potenciálních léčiv I." Master's thesis, 2020. http://www.nusl.cz/ntk/nusl-411576.
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Charles University Faculty of Pharmacy in Hradec Králové Department of Pharmaceutical Chemistry and Pharmaceutical Analysis Title of diploma thesis: Synthesis of thiazolidine-2,4-dione derivatives as potential drugs I Student: Anna Dušková Supervisor: PharmDr. Marta Kučerová, Ph.D. The theoretical part of this diploma thesis summarizes the biological activity of thiazolidine- 2,4-dione derivatives, focused mainly on their antibacterial, antimycobacterial and antifungal effects. The theoretical part shows that thiazolidine-2,4-dione derivatives are substances that have great potential to become good candidates for new drugs that are needed to be obtained due to the growing bacterial resistance to existing drugs. Thiazolidine-2,4-dione derivatives are already used in clinical practice as oral antidiabetics - pioglitazone and rosiglitazone. In the experimental part, I dealt with a three-step synthesis of (2,4-dioxothiazolidin-3-yl) acetic acid derivatives, which, however, was not succesful to prepare except for one product. This was followed by the synthesis of thiazolidine-2,4-dione derivatives, which consisted of the Knoevenagel condensation of thiazolidine-2,4-dione with aromatic and heterocyclic aldehydes, in which we managed to obtain a total of eight products. All substances were characterized...
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Yang, Shi-Qun, and 楊世群. "3-Acetyl-1，3-thiazolidine-2-thione." Thesis, 1988. http://ndltd.ncl.edu.tw/handle/84677009642886817755.
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Wang, Hui-Min, and 王惠民. "Utilization of derivatives of thiazolidine-2-thione." Thesis, 1988. http://ndltd.ncl.edu.tw/handle/57766773753850809928.
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Cheng, Yu-chi, and 鄭玉麒. "Synthesis and Characterization of Coumarin-based Organic Dye (4-Oxo-5-{5-[2-(1,1,6,6-tetramethyl-10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracen-9-yl)-benzothiazol-6-yl]-thiophen-2-ylmethylene}-2-thioxo-thiazolidin-3-yl)-acetic Acid." Thesis, 2008. http://ndltd.ncl.edu.tw/handle/59815753042855872033.
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碩士<br>國立臺灣科技大學<br>化學工程系<br>96<br>We reported here on the synthesis and photophysical properties of a no vel coumarin-based organic dye (14) as well as its application dye-sensiti zed nanocrystalline TiO2 solar cells (DSSCs).
The key step of the synthesis of new coumarin-based organic dye（14）for dye-sensitized solar cell as shown in scheme 1 ,is condensation reacti on of 2-Amino-5-bromobenzenethiol (3) and 3,3,3- triethoxypropionic ethyl ester (5) to give the corresponding (6-Bromo-benzothiazol-2-yl) - ac etic acid ethyl ester (6) in the presence of acetic acid and THF as solven t .Subsequent condensation with 8-hydroxy-1,1,7,7–tetramethyl -2, 3, 6,7 -tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde (9) gave 9- (6-Bromo-benzothiazol-2-yl)-1,1,6,6-tetramethyl -2, 3, 5, 6– tetrahydro- 1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one(10).Suzuki coupling reaction of the intermediate (10) with 2-thienyl-boronic acid in the presence of Pd(PPh3)4 and K2CO3 gave 1,1,6,6-tetramethyl-9 -(6-thiophen -2–yl-benzothiazol-2-yl)-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one(12). 5-[2-(1,1,6, 6-tetramethy l-10-oxo -2,3, 5,6 – tetrhydro-1H,4H,10H-11 -oxa-3a-a za-benzo[de] anthracen-9-yl) -3H – indol -5-yl]-thiophene-2-carbaldehyde (13) was synthesized from (12) by the Vilsmeyer-Haack reaction .An ethanolic solution including (13) and rhodanine- N-acetic acid was refluxed in the presence of piperidine for 24h.Purificat ion of the resulting precipitates by column chromatography to give deep b rown solids of the coumarin-based dye, (4-oxo -5-{5-[2 -(1,1,6,6- tetra methyl-10-oxo-2,3,5,6 -tetrahydro- 1H,4H,10H-11–oxa -3a-aza-benzo[de]anthracen- 9-yl) -benzothiazol-6-yl] –thiophen -2- ylmethylene}-2-thioxo-thiazolidin-3-yl) acetic acid(14).
A solar-energy-to-electricity conversion efficiency of 0.475％ was attained under AM 1.5 irradiation (100mW/cm2) it’s a Short Circuit Current density (Isc) of 0.403mA，an Open Circuit Voltage (Voc) of 0.502V，and a fill factor (FF) of 0.587.
This preliminary work suggests that the molecular-designed coumarin dye is promising in the application of DSSCS.
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WANG, HUI-MIN, та 王惠民. "1,3-THIAZOLIDINE-2-THIONE 衍生物的利用 CARBALKOXYLATION 與酯化". Thesis, 1988. http://ndltd.ncl.edu.tw/handle/18527207561502085902.
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Huang, Chong-Wei, and 黃崇偉. "Novel Organic Dye based on Thiazolidene applied in Organic Solar Cell." Thesis, 2014. http://ndltd.ncl.edu.tw/handle/rf9p96.
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碩士<br>國立臺灣海洋大學<br>光電科學研究所<br>102<br>This thesis is based on a series of D-A-A structure. Thiazolidene, the core molecule, produces P-type small molecules which through vacuum thermal evaporation can be made into organic solar cells; and with small molecular electron acceptor materials C60 and C70 together can be made into a heterojunction device.
In this project, DPPTPDC dye shown the greatest potential for solar cell use. By arranging different proportions of C60 or C70 monolayer heterojunction structures under AM1.5 solar illumination((100 mW/cm2), its efficiency can reach up to 1.55 %. Moreover, using it to produce a plane mixed bulk heterojunction of solar cell can further increase the power conversion efficiency(PCE) up to 2.63 %.
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Chiu, Hsiao-shan, and 邱筱珊. "Synthesis, Characterization and Crystal Engineering Structural Transformation of L-Thiazolidine-4-carboxylate-containing Homochiral Coordination Compounds." Thesis, 2013. http://ndltd.ncl.edu.tw/handle/28282970174106855902.
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碩士<br>國立中央大學<br>化學學系<br>101<br>This thesis focuses on the preparation of a series of metal complexes via the use of a combination of metal (Zn(II), Co(II), Ni(II), Cd(II) salts with a LTP (L-thiazolidine-4-carboxylate)) ligand under mild reaction conditions. Their structures were characterized by single-crystal X-ray diffraction analyses. The structures of the first series [M(LTP)2(H2O)2] (M = Zn(II) 1, Co(II) 2, Ni(II) 3) show that the metal ion is six-coordinated in a distorted octahedral geometry and bonded to two N and two O atoms from two LTP ligands with bis-chelating coordination mode and two water molecules. Hydrogen bonding interactions between the LTP ligand and the water molecule were observed to play an important role in the formation of their 3D hydrogen-bonded supramolecular architectures. The metal ion in the second series [M(LTP)2]n (M = Zn(II) 4) is five-coordinated, with a distorted trigonal bipyramidal geometry, bonded to two N and three O atoms from three LTP ligands. The metal ion in the third series of compounds [M(LTP)2]n (M = Zn(II) 5, Cd(II) 6) is six-coordinated in a distorted octahedral geometry, bonded to two N and four O atoms from four LTP ligands. In 4, one LTP ligand acts as a monodentate coordination mode through an O atom and the other two LTP ligands act as bis-chelating coordination modes through both N and O atoms with a metal ion to form a one-dimensional (1D) [Zn(LTP)2] chain. In 5 and 6, the two LTP ligands act as chelating agents through both N and O atoms and the other two LTP ligands are coordinated with metal ions via an O atom to form a two-dimensional (2D) wave-like network. These 2D layers are then arranged in an ABAB-type array via the intermolecular interactions of N-H×××S hydrogen bonds to form a 3D supramolecular architecture. The thermal stability of compounds 1-6 are studied by TGA analysis. In addition, in-situ PXRD measurements verify that the crystal engineering transformation of 1 to 4 and 1 to 5 in a major and minor product, respectively.
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YANG, SHI-GUN, та 楊世群. "3-Acetyl-1，3-thiazolidine-2-thione：一種具有高度選擇性的乙醯化試劑". Thesis, 1988. http://ndltd.ncl.edu.tw/handle/99291489600451345176.
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Lu, Hsueh-Yuan, and 呂學遠. "(I) Multicomponent Reaction Synthesis of Thiazolidine-Linked Benzimidazole Derivatives (II) Synthesis of Tetrahydroisoquinoline Heterocyclic Small Molecule Derivatives via Radical Pictet-Spengler Reaction." Thesis, 2019. http://ndltd.ncl.edu.tw/handle/feduqz.
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Vigia, Bruno Maurício. "Reações de Michael Assimétricas - Estudos Sintéticos e Computacionais." Master's thesis, 2022. http://hdl.handle.net/10316/99420.
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Dissertação de Mestrado em Química apresentada à Faculdade de Ciências e Tecnologia<br>As tiazolidinas são heterociclos de cinco membros que possuem as funções amina e tioéter e apresentam aplicações importantes em diversas áreas, nomeadamente, como ligandos quirais em reações de catálise enantiosseletiva. Estas unidades estão presentes em vários compostos naturais e bioativos, e são empregues na área da saúde, devido às propriedades farmacológicas conferidas pela presença do núcleo tiazolidínico. A versatilidade desta classe de compostos deu o mote para este trabalho que teve como objetivos a síntese e análise de tiazolidinas e a sua utilização em reações de Michael enantiosseletivas. Adicionalmente, pretendia-se estudar o mecanismo destas reações recorrendo a cálculos de estrutura eletrónica com o intuito de explicar e prever a enantiosseletividade.Uma primeira fase do trabalho centrou-se na síntese de uma variedade de tiazolidinas. Escolhemos como reagentes de partida, compostos naturais quirais disponíveis, a L-cisteína e o hidrocloreto do seu éster metílico e, por condensação com diversos aldeídos obtivemos um conjunto de ligandos tiazolidínicos com diferentes substituintes em C2.Numa segunda fase do nosso trabalho, os ligandos sintetizados foram ensaiados em reações de Michael assimétricas de ZnEt2 a chalconas, utilizando Ni(acac)2 como complexo precursor. Utilizando a (E)-1,3-difenil-2-propen-1-ona como substrato modelo, e as tiazolidinas derivadas do hidrocloreto do éster metílico da L-cisteína, ensaiámos a reação em tolueno e ciclo-hexano, solventes habitualmente referidos na literatura, e verificámos que havia conversões completas nos dois, embora os excessos enantioméricos, ee, fossem mais elevados em tolueno. De um modo geral obtiveram-se valores de ee baixos, tendo o mais elevado sido de 23 %. Os resultados obtidos permitiram tirar algumas conclusões acerca da influência, reatividade e seletividade, em função dos diferentes substituintes presentes na posição 2 do anel tiazolidínico. Um ligando com o grupo carboxilo em C4 derivado da L-cisteína foi também preparado e ensaiado na reação de Michael. A conversão observada foi completa, tendo-se, contudo, formado o produto racémico. Procedeu-se à alteração de algumas condições de reação, nomeadamente, temperatura de reação, e testaram-se outros nucleófilos, para além de ZnEt2, na presença e ausência de aditivos. Com as condições otimizadas, realizou-se a reação de Michael com outros substratos, para avaliar a abrangência do processo e poder concluir quanto à influência da estrutura dos substratos no resultado da reação. Verificámos que os produtos se formaram sempre com excesso do enantiómero R e que um menor impedimento estéreo no substrato, próximo do local de reação, parece favorecer uma maior seletividade.Do ponto de vista computacional, a otimização ao nível DFT das estruturas dos pré-estados de transição de um sistema catalítico tomado como sistema modelo, mostrou uma maior estabilidade dos complexos precursores da formação do enantiómero R em concordância com os dados obtidos experimentalmente.<br>Thiazolidines are five-membered heterocycles that have amine and thioether functions and have importante applications in areas, namely, as chiral ligands in enantioselective catalysis reactions. These units are presente in several natural and bioactive compounds, and are used in the health area, due to the pharmacological properties conferred by the presence of the thiazolidine nucleus. The versatility of this class of compounds set the tone for this work, which aimed at the synthesis and analysis of thiazolidines and their use in enantioselective Michael reactions. Additionally, we intended to study the mechanism of these reactions using electronic structure calculations in order to explain and predict enantioselectivity.A first phase of the work focused on the synthesis of a variety of thiazolidines. We chose as starting reagents, natural chiral compounds available, L-cysteine and the hydrochloride of its methyl ester and, by condensation with different aldehydes, we obtained a set of thiazolidine ligands with different substituents at C2.In a second phase of our work, the synthesized ligands were tested in asymmetric Michael reactions of ZnEt2 to chalcones, using Ni(acac)2 as precursor complex. Using (E)-1,3-diphenyl-2-propen-1-one as a model substrate, and the thiazolidines derived from L-cysteine methyl ester hydrochloride, we tested the reaction in toluene and cyclohexane, commonly referred solvents in the literature, and we found that there were complete conversions in both, although the enantiomeric excesses, ee, were higher in toluene. In general, low ee values were obtained, the highest being 23 %. The results obtained allowed us to draw some conclusions about the influence, reactivity and selectivity, depending on the different substituents presente in the 2-position of the thiazolidine ring. A ligand with the C4 carboxyl group derived from L-cysteine was also prepared and tested in the Michael reaction. The observed conversion was complete, however, the racemic product was formed. Some reaction conditions were changed, namely reaction temperature, and other nucleophiles were tested, in addition to ZnEt2, in the presence and absence of additives.With the optimized conditions, the Michael reaction was carried out with other substrates, to evaluate the scope of the process and to be able to conclude about the influence of the structure of the substrates on the reaction result. We found that the products were always formed with an excess of the R enantiomer and that a lower steric hindrance in the substrate, close to the reaction site, seems to favor greater selectivity.From the computacional point of view, the optimization at the DFT level of the structures of the pre-transition states of a catalytic system taken as a model system, showed a greater stability of the precursor complexes of the formation of the R enantiomer, in agreement with the data obtained experimentally.
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Koch, Gretchen M. Bollinger Joseph Martin. "Mechanistic analysis of the cystine lyase C-DES from Synechocystis sp. PCC 6803 stability of the [alpha]-aminoacrylate intermediate, formation of thiazolidine adduct and identity of the catalytic base /." 2009. http://etda.libraries.psu.edu/theses/approved/WorldWideIndex/ETD-4464/index.html.
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