Bibliografías temáticas / Pyrazolo[5

Literatura académica sobre el tema "Pyrazolo[5"

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Publicado: 1 de julio de 2022

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Artículos de revistas sobre el tema "Pyrazolo[5":

Abaszadeh, Mehdi, Hassan Sheibani y Kazem Saidi. "The Condensation of (Chlorocarbonyl)phenyl Ketene with Bisnucleophiles. Synthesis of 4-Hydroxy-5-phenylpyro-[2,3-c]pyrazol-6-ones and Formation of Pyrazolo[1,2-a]pyrazole-triones by Hydrogen Exchange in Unstable Mesoionic Compounds". Australian Journal of Chemistry 63, n.º 1 (2010): 92. http://dx.doi.org/10.1071/ch09344.

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The addition of (chlorocarbonyl)phenyl ketene 2 to 5-alkylpyrazol-3(4H)-ones 1 led to the formation of 3-hydroxypyrazolo[1,2-a]pyrazole-dione/pyrazolo[1,2-a]pyrazole-trione derivatives 3. This is ascribed to hydrogen exchange in initially formed unstable, mesoionic pyrazolo[1,2-a]pyrazol-4-ium-5-olates. In contrast, condensation of the same ketene with 3-alkyl-1-phenyl-2-pyrazolin-5-ones 4 afforded 4-hydroxy-3-alkyl-1,5-diphenylpyrano[2,3-c]pyrazol-6-one derivatives 5. The latter reaction provides a new and rapid route to 4-hydroxy-2-pyrones fused to pyrazole rings, in good to excellent yields.

Deeb, Ali, Medhat El-Mobayed, Abdel Naby Essawy, Adel Abd El-Hamid y Atef Mohamid Abd El-Hamid. "Heterocyclic synthesis from 3-amino-4-cyanopyrazole". Collection of Czechoslovak Chemical Communications 55, n.º 3 (1990): 728–33. http://dx.doi.org/10.1135/cccc19900728.

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3-Amino-4-cyanopyrazole I reacts with hydroxylamine and with hydrazine to yield 1H,6H-3-aminopyrazolo[3,4-c]pyrazole (III and IV). Diazotized IV couples with 2-naphthol to give the arylazo derivative VI which cyclizes to 9H-naphthol[2,1-e]pyrazolo[3',4':3,4]pyrazolo[5,1-c]-[1,2,4]triazine VII by means of acetic acid. The pyrazol-5-ylthiourea obtained from I and phenyl isothiocyanate undergoes base-catalyzed cyclization to give pyrazolo[3,4-d]pyrimidinethione derivative IX. Compound I reacts with cyclohexane in the presence of zinc chloride to give the tetrahydropyrazolo[3,4-b]quinoline derivative XI. The reaction of I with pyridine 1-oxide affords 4H,5H-pyrazolo[5',1':2,3] [1,2,4]triazolo[1,5-a]pyridine-3-carbonitrile XII.

Hosny, Mona A., Yasser H. Zaki, Wafaa A. Mokbel y Abdou O. Abdelhamid. "Synthesis, Characterization, Antimicrobial Activity and Anticancer of Some New Pyrazolo[1,5-a]pyrimidines and Pyrazolo[5,1-c]1,2,4-triazines". Medicinal Chemistry 16, n.º 6 (7 de septiembre de 2020): 750–60. http://dx.doi.org/10.2174/1573406415666190620144404.

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Background: Pyrazole and its derivatives are known to exhibit significant biological and pharmacological activities such as anticancer, anti-inflammatory, antioxidant, antibacterial, analgesic, antiviral, antimicrobial, antifungal, anti-glycemic, antiamoebic, and antidepressive. Considering the immense biological properties, pyrazole is one of the most widely studied nitrogen- containing heterocyclic nuclei. Fused pyrazole derivatives are composed of the pyrazole nucleus attached to other heterocyclic moieties. Objective: The objective of this article is the synthesis of some new pyrazolo[1,5-a]pyrimidine and pyrazolo[5,1-c]1,2,4-triazine derivatives with potential anticancer and antimicrobial activities. Methods: The in vitro growth inhibitory rates (%) and inhibitory growth activity (as measured by IC50) of the newly synthesized compounds were determined against the MCF-7 human breast carcinoma cell line in comparison with the well-known anticancer drug doxorubicin as the standard, using the MTT viability assay. The data generated were used to plot a dose-response curve from which the concentration (μM) of tested compounds required to kill 50% of the cell population (IC50) was determined. Cytotoxic activity was expressed as the mean IC50 of three independent experiments. The difference between inhibitory activities of all compounds with different concentrations was statistically significant p < 0.001. All compounds were structurally characterized by different spectroscopic techniques EI-MS, 1H-NMR, and 13C-NMR, and evaluated for their anticancer and antimicrobial activities (antibacterial and antifungal). Results: Several pyrazolo[1,5-a]pyrimidine derivatives were synthesized from the reaction of 2-(4- (5-amino-1H-pyrazol-3-yl)phenyl)-1H-indene-1,3(2H)-dione with the appropriate active methylene compounds in boiling ethanol. Also, pyrazolo[5,1-c]triazines were obtained through the reaction of 2-(4-(5-(chlorodiazenyl)-1H-pyrazol-3-yl)phenyl)-1H-indene-1,3(2H)-dione with various active methylene compounds in ethanol containing sodium acetate at 0-5 °C. The structures of the newly synthesized compounds were elucidated on the basis of elemental analysis, spectral data, and alternative synthetic routes whenever possible. The newly synthesized compounds were evaluated for their antitumor activity against a breast cancer cell line (MCF-7) and a human colon cancer cell line (HCT-116). The results revealed that the tested compounds showed high variation in the inhibitory growth rates and activities against the tested tumor cell lines. All newly synthesized compounds screen towards microorganisms e.g. Gram-negative bacteria, Gram-positive bacteria, and Fungi. Conclusions: 2-(4-(5-Amino-1H-pyrazol-3-yl)phenyl)isoindoline-1,3-dione proved to be a useful precursor for the synthesis of various pyrazolo[1,5-a]pyrimidine and pyrazolo[5,1-c]-1,2,4- triazines. The structures of the newly synthesized compounds were confirmed by spectral data and elemental analyses. The newly synthesized compounds were tested in vitro against the MCF-7, HCT-116 human cancer cell line and compared with doxorubicin as the standard, using the MTT viability assay. Most of the tested compounds were found to have moderate to high anticancer activity.

Elnagdi, Mohamed Hilmy, Ahmed Hafez Hussien Elghandour, Kamal Usef Sadek y Mahmoud Mohamed Mahfouz Ramiz. "Studies on Condensed Pyrazoles. A New Route for Synthesis of Pyrazolo[4,3-c]pyrazoles". Zeitschrift für Naturforschung B 44, n.º 8 (1 de agosto de 1989): 951–54. http://dx.doi.org/10.1515/znb-1989-0816.

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A novel synthesis of pyrazolo[4,3-c]pyrazoles via 1,5-dipolar cyclization of products of coupling of 2,3-dimethyl-1-phenyl-5-oxo-3-pyrazolin-4-diazonium chloride with active methylene reagents is reported.

Lindsay-Scott, Peter J. y Eloise Rivlin-Derrick. "Regiocontrolled Synthesis of 6,7-Dihydro-4H-pyrazolo[5,1-c][1,4]oxazines". Synthesis 52, n.º 01 (8 de octubre de 2019): 105–18. http://dx.doi.org/10.1055/s-0037-1610734.

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Synthetic access to 6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazines has been achieved in 3–4 steps from commercially available pyrazoles. Optimization of a protected hydroxyethyl group on N1 enabled the regiocontrolled construction of pyrazole-5-aldehydes in high yields; subsequent deprotection and reduction generated fused heterocyclic scaffolds bearing multiple substitution patterns. Moreover, the intermediate pyrazole lactols were shown to be versatile synthetic building blocks.

Abdelhamid, Abdou O., Zeineb H. Ismail y Anhar Abdel-Aziem. "Reactions with Hydrazonoyl Halides 601: Synthesis of Thieno[2′,3′:4,5] Pyrimidino[1,2-b][1,2,4,5]tetrazines, [1]benzothieno[2′,3′:4,5]pyrimidino [1,2-b][1,2,4,5]tetrazines, Pyrazolo[3′,4′:4,5]pyrimidino[1,2-b] [1,2,4,5]tetrazines and Pyrazolo[3,4-d]pyridazines". Journal of Chemical Research 2007, n.º 10 (octubre de 2007): 609–16. http://dx.doi.org/10.3184/030823407x256118.

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Thieno[2′,3′:4,5]pyrimidino[1,2- b][1,2,4,5]tetrazine, [1]benzothieno-[2′,3′:4,5]pyrimidino[1,2- b][1,2,4,5]tetrazine, pyrazolo [3′,4′:4,5]pyrimidino[1,2- b][1,2,4,5]tetrazine, triazolo[4,3- a]pyrimidin-5(1 H)-one, 1-{[2-(1-benzofuran-2-yl)-5-phenyl-4,5-dihydro-1 H-pyrazol-1-yl]-4-substituted-1,3-thiazol-5-yl}-2-phenyldiazene, 3-acyl-4-(1-benzofuran-2-ylcarbonyl) pyrazole and pyrazolo[3,4- d]pyridazine derivatives could be obtained via reactions of hydrazonoyl halides with the appropriate pyrimidine-2-thione, 3-amino-5,6-dimethyl-2-sulfanylthieno[2,3- d]pyrimidin-4(3 H)-one, 5-amino-6-mercapto-1-phenyl-1,5-dihydropyrazolo[3,4- d]pyrimidin-4-one and 1-(benzofuran-2-yl)-3-(dimethylamino)prop-2-en-1-one. Structures of the products have been determined by elemental analyses, spectral data studies and alternative synthesis whenever possible.

Forsyth, Craig M., Craig L. Francis, Saba Jahangiri, Andris J. Liepa, Michael V. Perkins y Anna P. Young. "N,N-Dialkyl-N'-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part VIII. Novel Pyrazolo-Fused Oxathiadiazines and Thiatriazoles". Australian Journal of Chemistry 63, n.º 4 (2010): 659. http://dx.doi.org/10.1071/ch09581.

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N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted with pyrazol-3-ones 2 under a variety of conditions to give pyrazolo[2,3-e][1,2,3,5]oxathiadiazine dioxides 3 and pyrazolo[3,2-b][1,4,3,5]oxathiadiazine dioxides 5, and frequently, one or both of pyrazolo[1,2-b][1,2,3,5]thiatriazole 1,1,5-trioxides 4 and 1,1,7-trioxides 6. In all reactions, the pyrazolo[3,2-b][1,4,3,5]oxathiadiazine 5 was the major product, with the pyrazolo[2,3-e][1,2,3,5]oxathiadiazine 3 being a significant product in the absence of base. Prior to our recent work, the core ring systems of compounds 3 and 5 had not been reported and compounds 4 and 6 are new derivatives of a rare ring system.

Norman, Rebecca E., Michael V. Perkins, Andris J. Liepa y Craig L. Francis. "N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIII. Cleavage and Rearrangement Reactions of Pyrazolo[1,5-b][1,2,4,6]thiatriazine 1,1-Dioxides". Australian Journal of Chemistry 69, n.º 1 (2016): 61. http://dx.doi.org/10.1071/ch15445.

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Treatment of pyrazolo[1,5-b][1,2,4,6]thiatriazines 1 with the Vilsmeier–Haack reagent afforded pyrazolo[1,5-a][1,3,5]triazines 5. Reaction of compounds 1 with trifluoroacetic anhydride, dimethyl sulfoxide, and triethylamine afforded 5-dimethylsulfanylidene derivatives 8. The guanidino-pyrazole-sulfonic acid 9 was produced from treatment of compounds 1 with trifluoroacetic acid under anhydrous conditions. Similar treatment in the presence of water afforded the desulfonated pyrazolo-guanidine 6. Reactions of 6 with one-carbon electrophiles provided various 4-substituted pyrazolo[1,5-a][1,3,5]triazines 5. Attempted catalytic hydrogenolysis of N7-benzyl pyrazolo[1,5-b][1,2,4,6]thiatriazines 2 in alcohols led to sulfamates 12 from thiatriazine ring cleavage. Ethyl acetate or tert-butanol as solvent allowed successful debenzylation to provide compounds 1. Aminolysis of compounds 2 gave sulfamides 13. Thermal rearrangement of compounds 2 afforded 6-benzyl-pyrazolo[3,4-e][1,2,4]thiadiazines 14.

Mokhonova, Inna D., Evgenij A. Maksimov, Irina V. Ledenyona, Alevtina Y. Yegorova y Khidmet S. Shikhaliev. "Reactions of 3H-furan-2-ones and 2H-chromen-2-ones with pyrazole-3(5)-diazonium salts". Heterocyclic Communications 24, n.º 4 (28 de agosto de 2018): 183–85. http://dx.doi.org/10.1515/hc-2017-0192.

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AbstractDerivatives of the new heterocyclic system, 6H-chromeno[4,3-e]pyrazolo[5,1-c][1,2,4]triazin-6-one, were obtained by the reaction of pyrazole-3(5)-diazonium salts with 4-hydroxy-2H-chromen-2-one. Similar reactions with 5-phenyl-3H-furan-2-one followed by intramolecular heterocyclization furnished 6-(4-halophenyl)-7-alkyl-2-phenylfuro[2,3-e]pyrazolo[5,1-c][1,2,4]triazines.

Abdelhamid, Abdou O., Victorin B. Baghos y Mervat M. A. Halim. "Synthesis and reactivity of N-[3-amino-4-(benzoxazol-2-yl)pyrazol-5-yl]phenylamine". Journal of Chemical Research 2007, n.º 7 (julio de 2007): 420–25. http://dx.doi.org/10.3184/030823407x228830.

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Pyrazolo[5,1- a]pyrimidines and pyrazolo[5,1-c][1,2,4]triazines containing benzooxazole moiety are synthesised from N-[3-amino-4-(benzoxazol-2-yl)pyrazol-5-yl]phenylamine or its diazonium chloride with the appropriate active methylene compounds. The newly synthesised compounds were elucidated by elemental analysis, spectral data and alternative synthetic route whenever possible.

Más fuentes

Tesis sobre el tema "Pyrazolo[5":

Ostache, Nicu-Carmin. "Synthèse et fonctionnalisation de bicycles 5-5 polyazotés : pyrazolo[3,4-d]thiazoles et pyrazolo[3,4-c]pyrazoles". Thesis, Orléans, 2019. http://intranet.univ-orleans.fr/bibliotheques/theses/nicu-cosmin-ostache_3378_vm.pdf/.

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Les structures bicycliques azotées sont parmi les entités les plus utilisées dans le domaine thérapeutique.Les bicycles 5:5 polyazotés sont des structures moins décrites que leurs analogues 6:6 ou6:5. Malgré le potentiel pharmacologique des pyrazolo [3,4-d] thiazoles et des pyrazolo [3,4-c] pyrazoles,deux exemples de ces familles rares, seuls quelques procédés de préparation et de fonctionnalisationdirecte de ces charpentes hétérocycliques sont décrits.De ce fait, l’objectif principal de nos recherches vise à développer de nouvelles voies de synthèse vers cesdeux charpentes bicycliques et ce, à partir de substrats facilement accessibles. Des stratégies efficaces ontété mises au point et s’appuient sur réactions de condensations avec des hydrazines, des N-cyclisationsintramoléculaires, des halogénations chimiosélectives et diverses réactions de couplage-croisé. De surcroît,le motif pyrazolo[3,4-d]thiazole a été fusionné à une structure triazapentalène, afin d’évaluer les propriétésspectroscopiques
Nitrogen-rich fused bicyclic structures are undisputedly one of the most used scaffolds for therapeutic use.The 5:5 polynitrogenated bicycles are moieties considerably less documented then their 6:6 or 6:5analogues. Despite the pharmacological potential of the pyrazolo[3,4-d]thiazoles and of thepyrazolo[3,4-c]pyrazoles, two examples of such rare families, only few methods of preparation and directfunctionalization of these heterocyclic moieties have been described.In this context, the main goal of our research aims at exploring new routes towards these bicyclic systemsfrom readily available and affordable starting materials. Efficient strategies were developed relying onhydrazine condensations, on intramolecular N-cyclizations, on chemo-selective halogenation and variouscross-coupling reactions. Moreover, the pyrazolo[3,4-d]thiazole entity was fused to a triazapentalenestructure in order to assess the spectroscopic properties

Bassoude, Ibtissam. "Synthèse de nouveaux dérivés pyrazolo[1,5-a]pyrimidiniques à visée biologique". Phd thesis, Université d'Orléans, 2012. http://tel.archives-ouvertes.fr/tel-00789954.

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Nos travaux de thèse portent sur la mise au point de nouvelles méthodes de synthèse permettant l'accès de façon rapide et efficace à différents dérivés pyrazolo[1,5-a]pyrimidiniques diversement fonctionnalisés.La première partie de ce travail concerne l'étude et l'application de la condensation de la pyran-2-one avec les 5(3)-amino-3(5)-arylpyrazoles que ce soit par chauffage classique ou sous irradiation micro-onde. Par la suite, un nouveau procédé d'(hétéro)arylation pallado-catalysé direct régiosélectif a été mis à profit pour élaborer des pyrazolo[1,5-a]pyrimidines fonctionnalisées tant en position 3 que sur le méthyle situé sur le sommet 7 de la 5,7-diméthylpyrazolo[1,5-a]pyrimidine.Le dernier volet de ce mémoire a été consacré à la préparation des entités pyrazolo[1,5-a]pyrimidiniques substituées en position 7 par des motifs benzyliques et ce, via une procédure " one-pot ", sous irradiation micro-onde, constituée d'une réaction d'arylation directe pallado-catalysée suivie d'une saponification-décarboxylation.

Laube, Markus. "Synthese von Cyclooxygenase-2-Inhibitoren als Grundlage für die funktionelle Charakterisierung der COX-2-Expression mittels PET". Doctoral thesis, Saechsische Landesbibliothek- Staats- und Universitaetsbibliothek Dresden, 2015. http://nbn-resolving.de/urn:nbn:de:bsz:14-qucosa-160091.

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Eine erhöhte COX-2-Expression wird bei Krankheiten wie rheumatoider Arthritis aber auch Parkinson, Alzheimer und Krebs beobachtet. Die nichtinvasive Visualisierung und Quantifizierung der COX 2-Expression in vivo mittels Positronen-Emissions-Tomographie (PET) könnte wertvolle Beiträge zur Diagnose dieser Krankheiten liefern. Zur Nutzung der PET-Technik werden geeignete COX-2-adressierende Radiotracer benötigt, deren Entwicklung auch die Identifizierung neuer, der Radiomarkierung zugänglicher COX-2-Inhibitoren als Leitstrukturen voraussetzt. Ziel dieser Arbeit war die Synthese von selektiven, der Radiomarkierung zugänglichen COX 2-Inhibitoren und deren In-vitro-Evaluierung, um Verbindungen zu identifizieren, die für eine weitere Entwicklung zu COX-2-adressierenden Radiotracern geeignet sind. Im Rahmen dieser Arbeit wurden ausgehend von literaturbekannten COX-2-Inhibitoren zwei grundlegende Strategien verfolgt: die Derivatisierung an der Peripherie sowie der Austausch von Strukturelementen im Grundgerüst der COX-2-selektiven Inhibitoren. In dieser Arbeit wird zum einen die Synthese der Zielverbindungen (Diphenyl-substituierte Indol-, Pyrazolo[1,5-b]pyridazin-, 1,2-Dihydropyrrolo[3,2,1-hi]indol- und Pyrrolo[3,2,1-hi]indol-Derivate sowie 2-Carbaboranyl-substituierte Indol-Derivate) und deren strukturanalytische Charakterisierung vorgestellt. Es konnte die McMurry-Cyclisierung als neuer Zugang für die Synthese von Carbaboranyl-substituierten Verbindungen und 1,2-Dihydropyrrolo[3,2,1-hi]indol-Derivaten sowie die Dehydrogenierung mittels DDQ als neue Variante zur Synthese von Pyrrolo[3,2,1-hi]indol-Derivaten etabliert werden. Durch Röntgeneinkristallstrukturanalyse wurde die Molekülstruktur von sechs Zwischenverbindungen und neun Zielverbindungen aufgeklärt. Zum anderen erfolgte die Charakterisierung der Verbindungen in vitro, wobei die COX-inhibitorischen Eigenschaften mit einem Fluoreszenz-basierten, einem Enzymimmunoassay (EIA)-basierten und einem [14C]Arachidonsäure-basierten COX-Assay bestimmt und zudem viele Verbindungen hinsichtlich ihrer Redoxeigenschaften untersucht wurden. Im Besonderen die hergestellten Indol-Derivate besitzen antioxidative Eigenschaften, die bei der Untersuchung der COX inhibitorischen Eigenschaften beachtet werden müssen. Die Derivatisierung an der Peripherie der bekannten Inhibitoren führte zur Identifizierung von zwei Aminosulfonyl-substituierten Indol-Derivaten und einem Fluorethoxy-substituierten Pyrazolo[1,5 b]pyridazin-Derivat, die grundsätzlich geeignete Kandidaten für eine weitere Entwicklung zum Radiotracer darstellen. Das Fluorethoxy-substituierte Pyrazolo[1,5 b]pyridazin-Derivat wurde im Rahmen dieser Arbeit mit Fluor-18 markiert und die initiale Charakterisierung des Radiotracers in vitro durchgeführt. Der Austausch von Strukturelementen im Grundgerüst der literaturbekannten COX-2-Inhibitoren mit voluminöseren Gruppen führte zum einen bei Austausch eines Phenylrings gegen einen Carbaboranyl-Cluster zum Verlust der COX-inhibitorischen Eigenschaften, was eine weitere Entwicklung dieser Verbindungen zum Radiotracer ausschließt. Zum anderen wurde ausgehend von 2,3-Diphenyl-1H-indol-Derivaten die bicyclische auf eine tricyclische Kernstruktur vergrößert. Dies lieferte hoch affine und selektive COX-2-Inhibitoren. Unter den hergestellten Verbindungen wurden ein 1,2-Dihydropyrrolo[3,2,1-hi]indol- und drei Pyrrolo[3,2,1-hi]indol-Derivate als vielversprechende Kandidaten für die weitere Entwicklung zum Radiotracer identifiziert.

Ejjoummany, Abdelaziz. "Design et fonctionnalisation d’hétérocycles originaux de type bicycliques [5-5] et tricycliques [6-5-6] à visée thérapeutique potentielle". Thesis, Orléans, 2020. http://www.theses.fr/2020ORLE3141.

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L’accès à de nouveaux composés hétérocycliques originaux biologiquement actifs, constitue l’un des principaux objectifs de notre groupe de recherche. Dans ce contexte, les travaux de cette thèse ont pour but principal, la conception de trois nouvelles familles de composés hétérocycliques contenant un motif pyrazolique susceptibles de présenter des activités biologiques, à savoir les pyrido[1',2':1,5]pyrazolo[4,3-d]pyrimidine, les pyrrolo[3,4-c]pyrazoles et les pyrazolo[5,1-b]thiazoles. Ce manuscrit est essentiellement dédié à un travail de méthodologie décrivant les différentes voies d’accès à ces hétérocycles originaux, tricycliques et bicycliques potentiellement modulables. La réactivité de ces synthons clés est ensuite étudiée avec divers procédés de fonctionnalisation palladocatalysés (Activation au PyBrOP-(hétéro)arylation, Liebeskind-Srogl, Suzuki-Miyaura, Buchwald-Hartwig, C-H arylation, substitution nucléophile aromatique) pour élaborer d’intéressantes chimiothèques construites autour de ces structures inédites, ouvrant ainsi de nombreuses perspectives pharmacologiques
The access to new original biologically active heterocyclic compounds, is one of the main objectives of our research group. In this context, the main purpose of this thesis is the design of three new families of heterocyclic compounds containing a pyrazolic motif that may exhibit biological activities, namely pyrido[1',2': 1.5]pyrazolo[4,3-d]pyrimidine, pyrrolo[3,4-c]pyrazole and pyrazolo[5,1-b]thiazole.This manuscript is essentially dedicated to a methodology work describing the different routes of access to these originals and potentially modular tricyclic and bicyclic precursors. The reactivity of these key synthons is then studied towards aromatic nucleophilic substitutions reactions and various pallado-catalyzed methods of functionalization (Activation with PyBrOP- (hetero) arylation, Liebeskind-Srogl, Suzuki-Miyaura, Buchwald-Hartwig, C-H arylation, aromatic nucleophilic substitution) to develop interesting libraries built around these unusual structures, thus opening numerous pharmacological perspectives

Bou, Karroum Nour. "Synthèse et développement de nouvelles molécules hétérocycliques tricycliques : étude de leurs propriétés immunomodulatrices". Thesis, Montpellier, 2018. http://www.theses.fr/2018MONTT014/document.

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Les récepteurs Toll-like 7 et 8 jouent un rôle important dans l’activation de la réponse immunitaire innée et adaptative. Leur stimulation conduit à la production des cytokines pro-inflammatoires et d’interférons de type I. L’imiquimod et son dérivé le résiquimod sont les premières molécules de faible poids moléculaire décrites comme agonistes du TLR7 et TLR8. Ces deux molécules ont montré des activités anticancéreuses et adjuvantes très importantes. Récemment, les TLR 7 et 8 ont fait l’objet de plusieurs publications visant à développer de nouveaux agonistes TLR7 et/ou TLR8 dans la perspective d’être utilisés comme adjuvants vaccinaux. Malgré les rôles essentiels de TLR7 et TLR8 dans la stimulation du système immunitaire, une activation immunitaire chronique peut être responsable de plusieurs maladies infectieuses et auto-immunes. D’où l’importance de développer également des antagonistes TLR7 et/ou TLR8.Ce travail de thèse est consacré à la synthèse et le développement de nouvelles molécules hétérocycliques, analogues de l’imiquimod et de résiquimod, dans le but d’identifier de nouveaux ligands TLR7 et/ou TLR8. Des voies de synthèse innovantes, permettant une modulation chimique importante grâce à des couplages croisés pallado-catalysés, ont été mises au point et ont permis d’obtenir une cinquantaine de molécules appartenant à trois séries chimiques différentes de type imidazo[1,2-a]pyrazine, imidazo[1,5-a]quinoxaline et pyrazolo[1,5-a]quinoxaline. De nombreux essais d’alkylation ont été tentés sur ces trois séries chimiques afin d’introduire une large variété de substituants sur le cycle à cinq sommets. L’application du couplage croisé de Sonogashira nous a permis d’établir une liaison C-C et introduire diverses chaines alkyles. Ces composés ont été testés pour leur activité agoniste et antagoniste TLR7 et 8. Aucun des composés cibles n'a présenté d’activité agoniste TLR7 et TLR8, dans l'intervalle des concentrations testées. Par contre, tous les composés ont montré une activité antagoniste sélective du TLR7. Les composés les plus actifs, 5.35a et 5.35b, membres de la série pyrazolo[1,5-a]quinoxaline ont montré des IC50 de l’ordre de 10 μM. Ces résultats prometteurs nous ont permis la découverte d’une activité antagoniste TLR7 importante pour la série pyrazolo[1,5-a]quinoxaline, une série très peu développée dans la littérature. La modulation chimique des molécules actives nous permet de donner naissance à de nouveaux leaders, qui peuvent jouer un rôle important dans la thérapie de plusieurs maladies infectieuses et auto-immunes
Toll-like receptors 7 and 8 play an important role in immune system activation. Their stimulation leads to the production of pro-inflammatory cytokines and type I interferons. Both receptors recognize viral ssRNA, as well as synthetic tricyclic imidazoquinoline derivatives such as imiquimod (TLR7 agonist) and resiquimod (TLR7/8 agonist). These two molecules showed significative anti-cancer and adjuvant activities. Many reports in the literature have been focused on the development of new TLR7/8 agonists belonging to different chemical series. These agonists strongly induce the production of T helper 1-polarizing cytokines and may therefore serve as promising candidate vaccine adjuvants. Despite the essential roles of TLR7 and TLR8 in the immune system stimulation, chronic immune activation may be responsible for several infectious and autoimmune diseases. Consequently, the development of TLR7 inhibitors may play an important role in the therapy of these diseases.In this study, we are interested in the synthesis and development of new heterocyclic molecules, analogs of imiquimod and resiquimod, in order to identify new TLR7 and/or TLR8 ligands. Different synthetic pathways have been developed, using cross coupling reactions, in order to obtain a wide variety of molecules belonging to three chemical series: imidazo[1,2-a]pyrazine, imidazo[1,5-a]quinoxaline et pyrazolo[1,5-a]quinoxaline. Various alkylation reactions were attempted on these three chemical series in order to introduce a wide variety of substituents on the five-membered ring. The application of Sonogashira's cross-coupling allowed us to establish a C-C bond and introduce various alkyl chains. All compounds have been tested for their TLR7/8 agonistic and antagonistic activity using HEK-Blue™-hTLR7/8 cells. The synthesized compounds are completely inactive as TLR7/8 agonists and are selective TLR7 antagonists. Two compounds of the pyrazolo[1,5-a]quinoxaline series, compound 5.35a and 5.35b, bearing butyl and isobutyl chain respectively, are potent and selective TLR7 antagonists with low micromolar IC50. Results allowed us to discover significative activity for the pyrazolo[1,5-a]quinoxaline series as selective TLR7 antagonists, which may therefore play an important role in the therapy of several infectious or autoimmune diseases

Belaroussi, Rabia. "Synthèse et fonctionnalisation de nouveaux dérivés tricycliques [6-5-6] polyhétéroaromatiques à visée thérapeutique potentielle". Thesis, Orléans, 2016. http://www.theses.fr/2016ORLE2002/document.

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La découverte de nouveaux candidats susceptibles de lutter contre différentes pathologies, en l’occurrence le cancer et les maladies neurodégénératives, constitue l’un des principaux objectifs de notre groupe de recherche. Dans ce contexte, les travaux de cette thèse ont pour but principal, la conception de deux nouvelles classes d’hétérocycles de structure planes, jusqu’à ce jour, très rarement étudiées, à savoir les pyrido[2’,1’ :1,5]pyrazolo[3,4-d]pyridazines et les pyrido[2’,1’ :1,5]pyrazolo[3,4-d]pyrimidines. Ce manuscrit est essentiellement dédié à un travail de méthodologie décrivant les différentes voies d’accès à ces originaux précurseurs tricycliques potentiellement modulables. La réactivité de ces synthons clés est ensuite étudiée vis-à-vis de réaction de substitutions nucléophiles aromatiques et de divers procédés de fonctionnalisation palladocatalysés (Suzuki-Miyaura, Buchwald-Hartwig, activation au PyBrOP-(hétéro)arylation) pour élaborer d’intéressantes chimiothèques construite autour de ces structures inédites ouvrant ainsi de nombreuses perspectives pharmacologiques
The discovery of new candidates to fight against various diseases, namely cancer and neurodegenerative diseases, is one of the main goals of our research group. In this context, the main purpose of this thesis, is the design of two new classes of heterocyclic planar structure, to date, rarely studied, namely pyrido[2’,1’ :1,5]pyrazolo[3,4-d]pyridazines and pyrido[2’,1’ :1,5]pyrazolo[3,4-d]pyrimidines. This manuscript is essentially dedicated to a methodology work describing the different routes of access to these originals and potentially modular tricyclic precursors. The reactivity of these key synthons is then studied towards aromatic nucleophilic substitutions reactions and various palladocatalyzed methods of functionalization (Suzuki-Miyaura, Buchwald-Hartwig, activation PyBrOP-(hetero) arylation) to develop interesting libraries built around these unusual structures, thus opening numerous pharmacologicals perspectives

Oleksik, Laurence. "Methodology for the synthesis of 4 or 5-substituted-3-perfluoroalkyl pyrazoles". Thesis, University of Leicester, 2004. http://hdl.handle.net/2381/30087.

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Initially the perfluoroacylation of a range of commercially available vinyl ethers and conversion of the resulting perfluoroacylated enol ethers to 1-H-pyrazoles via reaction with hydrazine is reported. The selective synthesis of a range of alpha-aryl vinyl ethers using Heck chemistry is then reported. Subsequent perfluoroacylations of the vinyl ethers followed by reaction of the resulting perfluoroacyl enol ethers with hydrazine affords a range of 5-aryl-3-perfluoroalkyl pyrazoles in good yields.;Alternative methodology for the synthesis of 5-aryl-3-perfluoroalkyl pyrazoles is then described in which resin bound esters are converted to vinyl ethers

Karahan, Dag Fulya. "Synthesis Of 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-1h-pyrazoles By Electrophilic Cyclization". Master's thesis, METU, 2011. http://etd.lib.metu.edu.tr/upload/12613443/index.pdf.

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Pyrazoles have been intensely studied in the design and synthesis of biologically active agents because they display considerable medicinal activities. Recent studies have shown that integration of a ferrocenyl unit with structural features of pyrazoles can result in the formation of the new products with enhanced or/and unexpected biological activity since several ferrocene derivatives have already been illustrated to be active against a number of tumors. Therefore, we have investigated the electrophilic cyclizations of the hydrazones to afford 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-substituted pyrazole derivatives. First, the requisite hydrazone derivatives were synthesized by the reactions of ferrocenyl propargyl aldehydes or ketones with a series of hydrazines. Then electrophilic cyclizations of these hydrazones were investigated by treating with 4-(nitrophenyl)sulfenyl chloride as electrophile. By employing these electrophilic cyclizations, a series of 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-1H-pyrazoles, 5-ferrocenyl-4-((4-nitrophenyl) sulfenyl)-3-methyl-1H-pyrazoles and 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-3-phenyl-1H-pyrazoles have been synthesized in moderate to good yields.

Rosales, Pauline Fagundes. "Bi-heterociclos a partir do Ácido Levulínico: Síntese de 5-[(5-(trifluormetil)-5-hidroxi-(3-substituido)-4,5-diidro-1H-pirazol-1-il)-1-propan-1-ona-3-il]-2-metil-7-trifluormetil)pirazolo[1,5-a]pirimidinas". Universidade Federal de Santa Maria, 2013. http://repositorio.ufsm.br/handle/1/10535.

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Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
An efficient method to obtain 2-methyl-5-(methylpropanoate-3-yl)-7-trifluoromethylpyrazolo[1,5-a]pyrimidine 2 from the reaction of compound methyl 7,7,7-trifluoro-4-methoxy-6-oxo-heptenoate with 3-amino-5-methyl-1H-pyrazol. This compound 2 brought to reaction with hydrazine monohydrate to obtain 2-methyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine-5-propanehydrazine 3 and after were later brought to cyclocondensation reaction with a series of β-alkoxyvinyltrifluoromethyl ketones giving the series of news bi-heterocyclic 5-[(5-(trifluoromethyl)-5-hydroxy- (3-substituted)-4,5-dihydro-1H-pyrazol-1-yl)-1-propan-1-one-3-yl]-2-methyl-7-trifluoro methyl)pyrazolo[1,5-a]pyrimidines compounds 5a-l. Compound 2-methyl-5-(methylpropanoate-3-yl)-7-trifluoromethylpyrazolo[1,5-a]pyrimidine 2 brought to transesterification reaction and hydrolises reaction for obtaining the compounds 6 and 7. The structures of all synthesized compounds were confirmed by 1H, 13C, 19F NMR data, and two-dimensional NMR techniques like HETCOR and COLOC, mass spectrometry data.
Este trabalho descreve um método eficiente para a obtenção de 2-metil-5-(propanoato-3-il de metila)-7-trifluormetilpirazolo[1,5-a]pirimidina 2 a partir da reação de ciclocondensação do composto 7,7,7-trifluor-4-metoxi-6-oxo-4-heptenoato de metila com 3-amino-5-metil-1H-pirazol. Este composto 2 foi levado à reação com monohidrato de hidrazina obtendo-se a 2-metil-7-trifluormetilpirazolo[1,5-a]pirimidina-5-propanohidrazina 3. Posteriormente, o composto 3 foi levado à reação de ciclocondensação do tipo [3+2] com uma série de β-alcoxivniltrifluormetil cetonas alquil e aril substituídas utilizando etanol como solvente, resultando em uma série de compostos bi-heterocíclicos inéditos 5-[(5-trifluormetil)-5-hidróxi-(3-substituidos)-4,5-diidro-1H-pirazol-1-il)-1-propan-1-ona-3-il]-2-metil-7-trifluormetilpirazolo[1,5-a]pirimidina 5a-l. O composto 2-metil-5-(propanoato-3-il de metila)-7-trifluormetilpirazolo[1,5-a]pirimidina 2 foi levado à reação de transesterificação e à reação de hidrólise para a formação dos respectivos compostos 6 e 7. As estruturas de todos os compostos sintetizados foram confirmadas por dados de RMN 1H, 13C, 19F e técnicas de RMN bidimensionais como HETCOR e COLOC, além de dados de espectrometria de massas.

Nadir, Saïd. "Complexes de l'acide 3, 5-pyrazole dicarboxylique : synthèses, études structurales, utilisation pour la préparation de céramiques conductrices". Lille 1, 1996. https://pepite-depot.univ-lille.fr/LIBRE/Th_Num/1996/50376-1996-182.pdf.

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La synthese de ceramiques oxydes conductrices, par reaction a l'etat solide, necessite des traitements a haute temperature. Une autre methode est d'utiliser des composes de coordination precurseurs pour la preparation de materiaux oxydes hautement disperses. Nous avons utilise l'acide 3,5-pyrazole dicarboxylique (dcph#3) qui se decompose a 300c ; ce diacide est potentiellement tetrachelatant. Nous avons obtenu des complexes stables avec une grande variete d'elements (cu, bi, vo, ba, pb, ni, co) ; ceux ci ont ete caracterises par a. T. G et par diffraction x a haute temperature. La structure cristalline du ligand (sous forme anhydre et hydratee) a ete determinee, l'etude structurale d'un complexe de nickel montre que dcph#3 se comporte comme un bidentate. Nous avons utilise la coprecipitation pour preparer des materiaux oxydes conducteurs en une seule etape par un traitement thermique approprie. Une synthese a ete aussi mise au point pour les oxydes conducteurs type bimevox recemment decouverts, tout comme les oxydes supraconducteurs yba#2cu#3o#7#-# ou (bi,pb)#2sr#2ca#2cu#3o#x. Une nouvelle famille d'oxydes mixtes a ete obtenue et caracterisee. La serie ba#2#-#xsr#xbio#4#+# adopte une structure type double perovskite, ou le bi presente un degre d'oxydation mixte (+iii, +v) et les cations alcalino terreux sont repartis dans les sites a et b du modele perovskite. La conductivite est majoritairement de type electronique.

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Capítulos de libros sobre el tema "Pyrazolo[5":

Pardasani, R. T. y P. Pardasani. "Magnetic properties of copper(II) complex of 5, 2-diphenyl-6H-pyrazolo-[1, 5-c] pyrimidine-7-thiones". En Magnetic Properties of Paramagnetic Compounds, 397–98. Berlin, Heidelberg: Springer Berlin Heidelberg, 2017. http://dx.doi.org/10.1007/978-3-662-49202-4_186.

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Pardasani, R. T. y P. Pardasani. "Magnetic properties of copper(II) complex of 5-(p-tolyl)-2-phenyl-6H-pyrazolo- [1, 5-c]pyrimidine-7-thione". En Magnetic Properties of Paramagnetic Compounds, 393–94. Berlin, Heidelberg: Springer Berlin Heidelberg, 2017. http://dx.doi.org/10.1007/978-3-662-49202-4_184.

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Pardasani, R. T. y P. Pardasani. "Magnetic properties of copper(II) complex of 5-(p-methoxyphenyl)-2-phenyl-6H-pyrazolo- [1, 5-c]pyrimidine-7-thiones". En Magnetic Properties of Paramagnetic Compounds, 395–96. Berlin, Heidelberg: Springer Berlin Heidelberg, 2017. http://dx.doi.org/10.1007/978-3-662-49202-4_185.

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Pardasani, R. T. y P. Pardasani. "Magnetic properties of copper(II) complex of 5-p-chlorophenyl-2-phenyl-6H-pyrazolo- [1, 5-c]pyrimidine-7-thiones". En Magnetic Properties of Paramagnetic Compounds, 399–400. Berlin, Heidelberg: Springer Berlin Heidelberg, 2017. http://dx.doi.org/10.1007/978-3-662-49202-4_187.

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Pardasani, R. T. y P. Pardasani. "Magnetic properties of copper(II) complex of 5-p-bromophenyl-2-phenyl-6H-pyrazolo- [1, 5-c]pyrimidine-7-thiones". En Magnetic Properties of Paramagnetic Compounds, 401–2. Berlin, Heidelberg: Springer Berlin Heidelberg, 2017. http://dx.doi.org/10.1007/978-3-662-49202-4_188.

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Lynch, Michael P., James R. Beck, Eddie V. P. Tao, James Aikins, George E. Babbitt, John R. Rizzo y T. William Waldrep. "1-Alkyl-5-cyano-1H-pyrazole-4-carboxamides". En ACS Symposium Series, 144–57. Washington, DC: American Chemical Society, 1991. http://dx.doi.org/10.1021/bk-1991-0443.ch012.

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ZELLER, JAMES R. "The Nitration of 5-Chloro-1,3-dimethyl-1H-pyrazole". En ACS Symposium Series, 107–14. Washington, D.C.: American Chemical Society, 1985. http://dx.doi.org/10.1021/bk-1985-0274.ch011.

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Hamper, Bruce C., Kindrick L. Leschinsky, Deborah A. Mischke y S. Douglas Prosch. "Chiral 3-Aryl-4-halo-5-(trifluoromethyl)pyrazoles". En ACS Symposium Series, 272–81. Washington, DC: American Chemical Society, 1999. http://dx.doi.org/10.1021/bk-2000-0746.ch019.

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Lynch, Michael P., Stephen A. Ackmann, Dale R. Heim, George E. Davis, Michael A. Staszak, James R. Beck, Edward E. Tschabold y Fred L. Wright. "Synthesis and Gametocidal Activity of 1-Aryl-5-(aminocarbonyl)-1H-pyrazole-4-carboxylic Acids". En Synthesis and Chemistry of Agrochemicals III, 200–211. Washington, DC: American Chemical Society, 1992. http://dx.doi.org/10.1021/bk-1992-0504.ch019.

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Pardasani, R. T. y P. Pardasani. "Magnetic properties of binuclear bis(acetylacetonato) chromium(III) complex bridged by pyrazole 3, 5-dicarboxylate". En Magnetic Properties of Paramagnetic Compounds, 1036–37. Berlin, Heidelberg: Springer Berlin Heidelberg, 2017. http://dx.doi.org/10.1007/978-3-662-49202-4_508.

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Actas de conferencias sobre el tema "Pyrazolo[5":

Jachak, Madhukar, Naresh Badgujar y Nilambari Yewalkar. "Reactions of 5-aminopyrazole with Active Methylene Compounds:Synthesis of Pyrazolo[3,4-b]pyridine Derivatives". En The 9th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2005. http://dx.doi.org/10.3390/ecsoc-9-01463.

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Shkineva, Tatyana, Irina Vatsadze y Igor Dalinger. "5-AMINO-3,4-DINITROPURAZOLE – A KEY SYNTHON FOR OBTAINING FUNCTIONALLY SUBSTITUTED PYRAZOLO[1,5-a]PYRIMIDINES". En Chemistry of nitro compounds and related nitrogen-oxygen systems. LLC MAKS Press, 2019. http://dx.doi.org/10.29003/m782.aks-2019/313-315.

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Gharib, Ali, Mina Roshani y Manouchehr Jahangir. "Efficient Catalytic Synthesis of Pyrazolo[3,4-d]pyrimidine, Pyrazolo[4,3- e][1,2,4]triazolo[1,5-c]pyrimidine, Pyrazolo[4,3-e][1,2,4]triazolo[1,5- c]pyrimidine, Pyrazolo[3,4-d]pyrimidin-4-one derivatives using Heterogeneous Preyssler Heteropolyacid, H₁₄[NaP₅W₃₀O₁₁0]/SiO₂". En The 13th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2009. http://dx.doi.org/10.3390/ecsoc-13-00169.

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Rozada, Thiago C., Michael J. V. da Silva, Rodrigo M. Pontes, Ernani A. Basso y Fernanda A. Rosa. "Theoretical study of the regiospecific synthesis of pyrazole-5- carboxylate from unsymmetrical enaminodiketones". En 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013104184411.

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Chandra, N. Srikantamurthy, E. A. Jithesh Babu, K. B. Umesha y M. Mahendra. "Synthesis and crystal structure studies of ethyl 5-methyl-1, 3-diphenyl-1H-pyrazole-4-carboxylate". En SOLID STATE PHYSICS: Proceedings of the 58th DAE Solid State Physics Symposium 2013. AIP Publishing LLC, 2014. http://dx.doi.org/10.1063/1.4872901.

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Medvedev, Michail, Michail Elinson y Alexey Ilovaisky. "Green approach to the design of functionalized medicinally privileged 4-aryl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile scaffold !" En The 15th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2011. http://dx.doi.org/10.3390/ecsoc-15-00580.

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Koalla, Rajesh, Chandan Ghorui, Shivanand Mangali, Naveen Periketi y A. K. Chaudhary. "Measurement of Refractive index and Absorption coefficient of 3, 4, 5 -Trinitro 1-H Pyrazole using Terahertz Time-domain Spectroscopy". En Frontiers in Optics. Washington, D.C.: OSA, 2021. http://dx.doi.org/10.1364/fio.2021.jw7a.58.

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Thomas, Andrew P., Maria-Elena Theoclitou, David Buttar, Linette Ruston, Gail Wrigley, Mike Dennis, David A. Rudge et al. "Abstract 3912: The discovery of AZD4547: An orally bioavailable, potent and selective N-(5-Pyrazolyl)benzamide FGFR1-3 inhibitor". En Proceedings: AACR 103rd Annual Meeting 2012‐‐ Mar 31‐Apr 4, 2012; Chicago, IL. American Association for Cancer Research, 2012. http://dx.doi.org/10.1158/1538-7445.am2012-3912.

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Cahyana, A. H., P. Salsabila, B. Ardiansah y D. U. C. Rahayu. "Magnetically recoverable Fe3O4@SiO2@Sm: Preparation and application in one-pot, three-component assembly of bis(phenyl-1H-pyrazol-5-ol) derivatives". En PROCEEDINGS OF THE 3RD INTERNATIONAL SYMPOSIUM ON CURRENT PROGRESS IN MATHEMATICS AND SCIENCES 2017 (ISCPMS2017). Author(s), 2018. http://dx.doi.org/10.1063/1.5064066.

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Rilak Simović, Ana, Dejan Lazić, Milica Međedović, Dušan Ćoćić y Biljana Petrović. "SYNTHESIS AND BIOLOGICAL ACTIVITY OF THE NEW PINCER TYPE RUTHENIUM(III) COMPLEX". En 1st INTERNATIONAL Conference on Chemo and BioInformatics. Institute for Information Technologies, University of Kragujevac, 2021. http://dx.doi.org/10.46793/iccbi21.316rs.

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We synthesized and characterized the ruthenium(III) pincer-type complex [RuCl3(H2Lt-Bu] (H2Lt- Bu = 2,6-bis(5-tert-butyl-1H-pyrazol-3-yl)pyridine, 1) by elemental analysis, IR and UV-Vis spectroscopy, and mass spectrometry (MS) method ESI Q-TOF. For comparison reason, we also studied ruthenium(III) terpyridine complexes of the general formula [Ru(N-N-N)Cl3] where N-N-N = 4′-chloro- terpyridine (Cl-tpy; 2) or 4′-chlorophenyl-terpyridine (Cl-Ph-tpy; 3). Kinetic study of the substitution reactions of 1–3 with biomolecules showed that the rate constants depend on the properties of the spectator ligand and the nature of the entering nucleophile. To gain further insight into the reactivity of ruthenium complexes with potential biological targets, we examined the interactions of 1 – 3 with DNA and HSA. The DNA/HSA binding study showed that in comparison to complex 1 (bis– pyrazolylpyridine), the other two (2 and 3) terpyridine complexes had a slightly better binding affinity to calf thymus DNA (CT DNA), while in the case of human serum albumin (HSA), complex 1 exhibited the most strong quenching ability.