Relevant bibliographies by topics / Aminophosphonates

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  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters
  4. Conference papers

Academic literature on the topic 'Aminophosphonates'

Author: Grafiati
Published: 4 June 2021
Last updated: 6 September 2023

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Journal articles on the topic "Aminophosphonates"

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Varga, Petra R., Rita Oláhné Szabó, György Dormán, Szilvia Bősze, and György Keglevich. "Cytotoxic Activity of α-Aminophosphonic Derivatives Coming from the Tandem Kabachnik–Fields Reaction and Acylation." Pharmaceuticals 16, no. 4 (March 28, 2023): 506. http://dx.doi.org/10.3390/ph16040506.

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Encouraged by the significant cytotoxic activity of simple α-aminophosphonates, a molecular library comprising phosphonoylmethyl- and phosphinoylmethyl-α-aminophosphonates, a tris derivative, and N-acylated species was established. The promising aminophosphonate derivatives were subjected to a comparative structure–activity analysis. We evaluated 12 new aminophosphonate derivatives on tumor cell cultures of different tissue origins (skin, lung, breast, and prostate). Several derivatives showed pronounced, even selective cytostatic effects. According to IC50 values, phosphinoylmethyl-aminophosphonate derivative 2e elicited a significant cytostatic effect on breast adenocarcinoma cells, but it was even more effective against prostatic carcinoma cells. Based on our data, these new compounds exhibited promising antitumor activity on different tumor types, and they might represent a new group of alternative chemotherapeutic agents.
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Kleszczyńska, Halina, Dorota Bonarska, Janusz Sarapuk, and Krzysztof Bielecki. "Physiological Activity of Some Organophosphorous Compounds and Their Influence on Mechanical Properties of Erythrocytes." Zeitschrift für Naturforschung C 56, no. 11-12 (December 1, 2001): 999–1002. http://dx.doi.org/10.1515/znc-2001-11-1216.

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Abstract Hemolysis and fluidization of erythrocytes (RBC) membranes by some newly synthesized aminophosphonates as well as their potency to induce electrolyte efflux from cucumber (Cu­cumis sativus cv "Wisconsin") cotyledons were studied. Also, the chlorophyll content in aminophosphonate-treated cotyledons was affected. The compounds studied differed mainly in hydrophobicity of their substituents at the carbon, nitrogen and phosphorus atoms. It was found that aminophosphonate potency to fluidize RBC membranes depended on the combination of its overall lipophilicity and/or the kind of substituent at the P atom. Espe­cially, iso-propyl groups enhanced that potency. The sequence of am inophosphonates that exhibited the strongest fluidization activity was paralelled by their physiological and hem o­ lytic activities; in the latter case for these compounds that hemolyzed RBC under used con­ centrations. A general conclusion is that both the stereochemistry and lipophilicity determine the effi­ciency of the aminophosphonates studied. This efficiency is most probably related to the interaction of aminophosphonates with the lipid phase of biological objects.
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Rassukana, Yulia, Ivanna Yelenich, and Petro Onysʹko. "Fluorinated NH-iminophosphonates in synthesis of biorelevant α-aminophosphonic acids derivatives." Ukr. Bioorg. Acta 2022, Vol. 17, N1 17, no. 1 (June 30, 2022): 101–4. http://dx.doi.org/10.15407/bioorganica2022.01.101.

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Reactions of (poly)fluoroalkylated NH-iminophosphonates with nitromethane, trimethylsilylcyanide, and diphenylphosphine oxide lead to respective fluorinated β-nitro-α-aminophosphonates, α-cyano-α-aminophosphonates, and heminal bisphosphonates. Reaction with 3-aminocrotonitrile 5 proceds at the β-position of enamine. In the case of α-imino chlorodifluoroethylphosphonate 1c the reaction is accompanied by an unusual nucleophilic substitution of the chlorine atom in CF2Cl group with the formation of pyrroline bearing a difluoromethylated aminophosphonate moiety
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Wątroba, Karolina, Małgorzata Pawełczak, and Marcin Kaźmierczak. "Dipeptide analogues of fluorinated aminophosphonic acid sodium salts as moderate competitive inhibitors of cathepsin C." Beilstein Journal of Organic Chemistry 19 (April 12, 2023): 434–39. http://dx.doi.org/10.3762/bjoc.19.33.

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In this paper, we present the solvolysis reaction of dipeptide analogues of fluorinated aminophosphonates with simultaneous quantitative deprotection of the amino group. To the best of our knowledge, this work is the first reported example of the application of fluorinated aminophosphonates in cathepsin C inhibition studies. The new molecules show moderate inhibition of the cathepsin C enzyme, which opens the door to consider them as potential therapeutic agents. Overall, our findings provide a new avenue for the development of fluorinated aminophosphonate-based inhibitors.
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Kocsis, Dorottya, Petra Regina Varga, Rusul Keshwan, Mina Nader, Miléna Lengyel, Pál Szabó, István Antal, Károly Kánai, György Keglevich, and Franciska Erdő. "Transdermal Delivery of α-Aminophosphonates as Semisolid Formulations—An In Vitro-Ex Vivo Study." Pharmaceutics 15, no. 5 (May 11, 2023): 1464. http://dx.doi.org/10.3390/pharmaceutics15051464.

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α-Aminophosphonates are organophosphorus compounds with an obvious similarity with α-amino acids. Owing to their biological and pharmacological characteristics, they have attracted the attention of many medicinal chemists. α-Aminophosphonates are known to exhibit antiviral, antitumor, antimicrobial, antioxidant and antibacterial activities, which can all be important in pathological dermatological conditions. However, their ADMET properties are not well studied. The aim of the current study was to provide preliminary information about the skin penetration of three preselected α-aminophosphonates when applying them as topical cream formulations in static and dynamic diffusion chambers. The results indicate that aminophosphonate 1a, without any substituent in the para position, shows the best release from the formulation and the highest absorption through the excised skin. However, based on our previous study, the in vitro pharmacological potency was higher in the case of para-substituted molecules 1b and 1c. The particle size and rheological studies revealed that the 2% cream of aminophosphonate 1a was the most homogenous formulation. In conclusion, the most promising molecule was 1a, but further experiments are proposed to uncover the possible transporter interactions in the skin, optimize the topical formulations and improve PK/PD profiles in case of transdermal delivery.
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Kiss, Tamas, István Lázár, and Pawel Kafarski. "Chelating Tendencies of Bioactive Aminophosphonates." Metal-Based Drugs 1, no. 2-3 (January 1, 1994): 247–64. http://dx.doi.org/10.1155/mbd.1994.247.

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The metal-binding abilities of a wide variety of bioactive aminophosphonates, from the simple aminoethanephosphonic acids to the rather large macrocyclic polyaza derivatives, are discussed with special emphasis on a comparison of the analogous carboxylic acid and phosphonic acid systems. Examples are given of the biological importance of metal ion – aminophosphonate interactions in living systems, and also of their actual and potential applicability in medicine.
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Kraicheva, Ivanka, Georgi Momekov, Rositsa Mihaylova, Margarita Topashka-Ancheva, Ivelina Tsacheva, Ivanka Stoineva, Elitsa Vodenicharova, and Paraskev Nedialkov. "Synthesis of Two Novel Homologous Polyphosphoesters Containing Aminophosphonate Units and Cytotoxicity of Some Low-Molecular and Polymeric Aminophosphonate Derivatives." Advances in Materials Science and Engineering 2018 (August 13, 2018): 1–8. http://dx.doi.org/10.1155/2018/9565401.

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Two novel polyphosphoesters containing anthracene- and furan-derived aminophosphonate moieties, namely, poly[oxyethylene(aminophosphonate-co-H-phosphonate)]s P-12 and P-13, were synthesized through an addition of poly(oxyethylene H-phosphonate) to 9-anthrylidene-furfurylamine and characterized. The novel polyphosphoester P-12 and a series of previously described anthracene-derived compounds including Schiff bases S-1 and S-2, α-aminophosphonates A-3–A-6, bis-aminophosphonate B-6, two enantiomers A-5a and A-5b, and polyphosphoesters P-8–P-11 containing aminophosphonate units were screened for antitumor activity against a panel of human leukemic cell lines, using cisplatin as a reference cytotoxic agent. As concluded from the cytotoxicity assays, both precursors S-1 and S-2 presented similar cytotoxicity profiles that are cisplatin-like only in the REH cell line. Leader compound of the α-aminophosphonates is A-4 with cell death-inducing properties fully equaling those of the referent drug in all of the screened leukemic cell lines with the only exception being the AML histological subtype HL-60. Some of the polymeric analogues elicited moderate (P-10 and P-12) to low (P-11) cytotoxic activity, whereas the polyphosphoesters P-8 and P-9 produced in vitro antitumor effects largely surpassing cisplatin’s. The compounds P-8, P-9, and A-4 could be potential new materials for anticancer therapeutic purposed.
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Canepa, Paolo, Danijela Gregurec, Nara Liessi, Silvia Maria Cristina Rotondi, Sergio Enrique Moya, Enrico Millo, Maurizio Canepa, and Ornella Cavalleri. "Biofunctionalization of Porous Titanium Oxide through Amino Acid Coupling for Biomaterial Design." Materials 16, no. 2 (January 13, 2023): 784. http://dx.doi.org/10.3390/ma16020784.

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Porous transition metal oxides are widely studied as biocompatible materials for the development of prosthetic implants. Resurfacing the oxide to improve the antibacterial properties of the material is still an open issue, as infections remain a major cause of implant failure. We investigated the functionalization of porous titanium oxide obtained by anodic oxidation with amino acids (Leucine) as a first step to couple antimicrobial peptides to the oxide surface. We adopted a two-step molecular deposition process as follows: self-assembly of aminophosphonates to titanium oxide followed by covalent coupling of Fmoc-Leucine to aminophosphonates. Molecular deposition was investigated step-by-step by Atomic Force Microscopy (AFM) and X-ray Photoemission Spectroscopy (XPS). Since the inherent high roughness of porous titanium hampers the analysis of molecular orientation on the surface, we resorted to parallel experiments on flat titanium oxide thin films. AFM nanoshaving experiments on aminophosphonates deposited on flat TiO2 indicate the formation of an aminophosphonate monolayer while angle-resolved XPS analysis gives evidence of the formation of an oriented monolayer exposing the amine groups. The availability of the amine groups at the outer interface of the monolayer was confirmed on both flat and porous substrates by the following successful coupling with Fmoc-Leucine, as indicated by high-resolution XPS analysis.
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del Corte, Xabier, Aitor Maestro, Adrián López-Francés, Francisco Palacios, and Javier Vicario. "Synthesis of Tetrasubstituted Phosphorus Analogs of Aspartic Acid as Antiproliferative Agents." Molecules 27, no. 22 (November 18, 2022): 8024. http://dx.doi.org/10.3390/molecules27228024.

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An efficient general method for the synthesis of a wide family of α-aminophosphonate analogs of aspartic acid bearing tetrasubstituted carbons is reported through an aza-Reformatsky reaction of α-iminophosphonates, generated from α-aminophosphonates, in an umpolung process. In addition, the α-aminophosphonate substrates showed in vitro cytotoxicity, inhibiting the growth of carcinoma human tumor cell lines A549 (carcinomic human alveolar basal epithelial cell) and SKOV3 (human ovarian carcinoma). In view of the possibilities in the diversity of the substituents that offer the synthetic methodology, an extensive profile structure–activity is presented, measuring IC50 values up to 0.34 µM in the A549 and 9.8 µM in SKOV3 cell lines.
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Rogacz, Diana, Jarosław Lewkowski, Zbigniew Malinowski, Agnieszka Matusiak, Marta Morawska, and Piotr Rychter. "Effect of New Thiophene-Derived Aminophosphonic Derivatives on Growth of Terrestrial Plants. Part 2. Their Ecotoxicological Impact and Phytotoxicity Test Toward Herbicidal Application in Agriculture." Molecules 23, no. 12 (December 1, 2018): 3173. http://dx.doi.org/10.3390/molecules23123173.

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Background: The aim of this work was to evaluate phytotoxicity of the thiophene derivatives against three persistent weeds of a high degree of resistance (Galinsoga parviflora Cav., Rumex acetosa L., and Chenopodium album) as well as their ecotoxicological impact on Heterocypris incongruens. In addition, Aliivibrio fischeri was measured. Two of eight described aminophosphonates, namely dimethyl N-(2-methoxyphenyl)amino(2-thienyl)methylphosphonate (2d) and dimethyl N-(tert-butyl)- (2-thienyl)methylphosphonate (2h), have never been reported before. Methods: The phytotoxicity of tested aminophosphonates toward their potential application as soil-applied herbicides was evaluated according to the OECD 208 Guideline. Ecotoxicological properties of investigated compounds were made using the OSTRACODTOXKITTM and Microtox® tests. Results: Obtained results showed that four aminophosphonates have interesting herbicidal properties and N-(2-methylphenyl)amino- (2-thienyl)methylphosphonate (2a) was found to kill efficiently the most resistant plant Chenopodium album. None of the tested compounds showed important toxicity against Aliivibrio fischeri. However, their toxic impact on Heterocypris incongruens was significantly elevated. Conclusions: The aminophosphonate 2a showed herbicidal potential and it is not toxic against tested bacteria (EC50 over 1000 mg/L). It was found to be moderately toxic against ostracods [mortality 48% at 10 mg/kg of soil dry weight (s.d.w.)] and this problem should be solved by the use of the controlled release from a polymeric carrier.
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Dissertations / Theses on the topic "Aminophosphonates"

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Adler, Pauline. "Réactivité des alpha-amino allénylphosphonates : des amino vinylphosphonates aux spirodiénones lactames." Thesis, Université Paris-Saclay (ComUE), 2016. http://www.theses.fr/2016SACLS209.

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Ces dernières années, les aminophosphonates, analogues des acides aminés, ont suscité un vif intérêt. En effet, ces composés présentent un large éventail d'activités biologiques. Récemment, une nouvelle approche pour la préparation des aminophosphonates a été développée, basée sur la réduction asymétrique des amino vinylphosphonates (AVPs). Bien que de nombreuses synthèses d’AVPs soient rapportées dans la littérature, leur application sur large échelle et la possibilité d’avoir une grande diversité de substituants restent un défi. C’est ce qui nous a conduits à préparer stéréosélectivement des alpha-AVPs. Nous avons développé une synthèse courte, efficace et stéréosélective pour accéder à ces composés. La première partie de ce travail a été le développement d'une synthèse efficace des alpha-amino allénylphosphonates (AAPs) afin d’étudier leur réduction en AVPs. Le second défi a été la réduction chimio- et stéréosélective des AAPs en AVPs. Nous avons établi des règles afin de prédire la stéréosélectivité de cette réduction qui dépend de la substitution sur l’allène, le groupement phosphonate et sur l'atome d'azote afin de préparer, au choix, l’AVP de configuration (Z) ou (E).Comme alternative à cette réduction chimique, nous avons entrepris une étude électrochimique sur nos substrats (Collaboration avec Pr. Pedro de Oliveira, Université Paris Sud). Nous avons montré que nous étions en mesure de réduire chimiosélectivement les AAPs en amino allylphosphonates. Afin d'élargir notre catalogue d’AVPs, nous avons étudié la réactivité des AVPs vis à vis des réactions de métathèse (Collaboration avec Dr. Joëlle Prunet, University of Glasgow). Nous avons développé une synthèse courte qui nous donne accès à de nouveaux AVPs cycliques. Enfin, dans le cadre de notre étude, nous nous sommes intéressés au traitement oxydant de nos AAPs protégés par un groupement para-méthoxybenzyle. Cela nous a permis de préparer trois types d’azaspirodiénones différents. Une étude approfondie du mécanisme a été entreprise
In the past few years, aminophosphonates have attracted considerable attention due to their use as analogues of aminoacids. These compounds show a wide range of biological activities. Recently a new approach for the preparation of aminophosphonates, based on the asymmetric reduction of amino vinylphosphonates (AVPs), has been developed. Although several synthesis of AVPs are reported in the literature, their applicability to large scale and with a large diversity of substituents remains a challenge. This observation led us to stereoselectively prepare alpha-AVPs. We developed a short, efficient and stereoselective synthesis to access these AVPs. The first part of the work was the development of an efficient synthesis of alpha-amino allenylphosphonates (AAPs) to investigate their reduction as AVPs.The following challenge was the chemo- and stereoselective reduction of the AAPs into AVPs. We have established some rules to predict the stereoselectivity of this reduction, depending on the substitution on the allenyl moiety, on the phosphonate group and on the nitrogen atom in order to prepare either the (E)- or the (Z)-AVP.As an alternative to this chemical reduction, we started an electrochemical study on our substrates (Collaboration with Pr. Pedro de Oliveira, Université Paris Sud). We showed that we were able to chemoselectively reduce the AAPs into amino allylphosphonates. In order to enlarge our catalog of AVPs, we studied the reactivity of AVPs towards the metathesis reaction (Collaboration with Dr. Joëlle Prunet, University of Glasgow). We developed a short synthesis that gives us access to new cyclic AVPs. In the course of our studies on AAPs, we explored their reactivities towards oxidation. This led us to prepare three different types of azaspirodienones. A comprehensive study of the mechanism has been undertaken
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Perez, Vincent. "Synthèses sélectives d’isoxazolines et isoxazoles phosphonates : compétition de C- vs. O-alkylation et cycloadditions d’ynamido-phosphonates." Thesis, Université Paris-Saclay (ComUE), 2017. http://www.theses.fr/2017SACLS363.

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En raison de la vaste gamme d'activités biologiques qu'ils possèdent, les aminophosphonates cycliques ont attiré l’attention des chimistes et des biologistes. La synthèse d’hétérocycles substitués par un atome de phosphore a largement été rapportée dans la littérature. Dans ce contexte, le premier défi a été de proposer une nouvelle voie d'accès au motif 5-phosphono-isoxazoline. Une méthodologie a été développée, reposant sur la formation de N-oxydes d’isoxazolines par réaction de O-alkylation d’un ion nitronate sur un composé α-substitué vinylphosphonate, suivie d’une réduction pour former les composés attendus. La réaction de O-alkylation a notamment fait l’objet d’une étude approfondie pour donner de manière exclusive le N-oxyde d’isoxazoline. Bien que les ynamides aient été largement décrits dans la littérature, la synthèse et la réactivité des ynamido-phosphonates ont quant à elles très peu été étudiées. Le deuxième défi a consisté à trouver une nouvelle approche de formation des ynamido-phosphonates par couplage cupro-catalysé à partir d’un bromoalcynylphosphonate préalablement synthétisé. Ensuite, la réactivité de ces ynamido-phosphonates a été étudiée dans le but de former des isoxazoles substitués par un atome de phosphore et d’azote. Des réactions de cycloaddition [1,3]-dipolaire sur ces ynamides ont été entreprises. Enfin, l’oxydation de ces ynamides a permis d’accéder à de nouveaux motifs phosphonospirodiénones lactames
Due to the wide range of biological activities that they show, cyclic aminophosphonates have attracted attention of the chemists and biologists. Hence, the synthesis of heterocycles substituted with a phosphorus atom has been reported in the literature. In this context, our first challenge was to propose a new route to access the 5-phosphono isoxazoline motif. A methodology was developed based on the formation of isoxazoline N-oxide through an O-alkylation reaction of a nitronate anion to α-substituted vinylphosphonate, followed by a reduction to form the expected product. The O-alkylation reaction was investigated to give exclusively the isoxazoline N-oxide. Although the chemistry of ynamides has been widely reported in the literature, the synthesis and reactivity of ynamido-phosphonates is less documented. Our second challenge consisted to find a new approach to synthesize ynamido-phosphonates using a copper catalyzed coupling reaction with a bromoalkynylphospnates previously formed. Next, the reactivity of these compounds was studied. In order to form isoxazoles substituted with a phosphorus and nitrogen atom, [1,3]-dipolar cycloaddition reactions have been studied with these ynamido-phosphonates. Finally, the oxidation of these ynamido-phosphonates was studied and it gave us access to new phosphonospirodienone lactams
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Roubaud, Valérie. "Synthèse de (pyrrolidin-2-YL)phosphonates dialkyliques par aminomercuration d'alcenyl alpha-aminophosphonates." Aix-Marseille 1, 1994. http://www.theses.fr/1994AIX11015.

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Au cours de ce travail, une voie originale d'acces aux (pyrrolidin-2-yl) phosphonates dialkyliques par aminomercuration d'alcenyl alpha-aminophosphonates a ete developpee. Il a ete montre que cette reaction est regio et stereoselective ; a partir d'aminophosphonates gamaethyleniques, seule la formation des diastereoisomere des cycles pyrrolidiniques a ete observee. En effectuant des suivis par rmn de l'aminomercuration d'alcenyl alpha-aminophosphonates, nous avons montre que dans tous les cas la conversion en mercurique cyclique intermediaire est totale. La reduction de ce mercurique intermediaire par le borohydrure de sodium conduit aux pyrrolidines attendues. Toutefois une proportion variable du mercurique est transformee en aminophosphonate de depart. En accord avec les donnees de la litterature, nous avons confirme par des experiences de piegeages rpe la participation d'un mecanisme radicalaire lors de cette etape de reduction, le retour au point de depart s'expliquant par un mecanisme de beta-scission du radical alkyle intermediaire. La determination de la geometrie d'un diastereoisomere par diffraction des rx et l'analyse rmn#1h, #1#3c et #3#1p de l'ensemble des pyrrolidines obtenues, avant et apres reduction, nous a permis d'etablir leur stereochimie. Nous avons etudie les conformations privilegiees d'un diastereoisomere pyrrolidinique par une etude rmn jointe a des calculs de mecanique moleculaire. L'oxydation de couples de diastereoisomeres de (pyrrolidin-2-yl) phosphonates dialkyliques de stereochimie connue a montre que les nitroxydes correspondants presentaient une difference de persistance significative. Celle-ci s'explique par une difference d'accessibilite de l'hydrogene porte par les carbones en alpha du centre radicalaire; cet hydrogene etant implique dans la reaction de dismutation qui constitue le principal mode de disparition du radical
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Tesson, Nicolas. "Synthèse stéréosélective rapide des acides aminocyclopropanephosphoniques et d'analogues biologiquement actifs." Paris 11, 2001. http://www.theses.fr/2001PA112220.

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Baccari, Zayed [Verfasser]. "Synthèse, propriétés complexantes et activités biologiques de nouveaux α-aminophosphonates et α-hydroxyphosphonates / Zayed Baccari." München : GRIN Verlag, 2019. http://d-nb.info/1180623762/34.

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Rana, K. C. "Design and synthesis of aminophosphonates as protease inhibitors and development of new synthetically useful methodologies." Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 2011. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/3782.

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Charbonnier-Gérardin, Christine. "Nouvelles applications en synthèse des acides 2-dialkylphosphonoalcanoique : préparation de phosphonopeptides inhibiteurs de peptidases." Nancy 1, 1991. http://www.theses.fr/1991NAN10063.

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Une conception générale de synthèse de phosphonopeptides renfermant un motif phosphore du cote c-terminal ou du cote n-terminal est proposée à partir d'un même substrat acide 2-dialkylphosphonoalcanoique. L'objectif est de préparer des inhibiteurs de peptidases présentant une activité thérapeutique. L'approche la plus efficace pour introduire le motif phosphonate sous forme enantiomeriquement pure dans les phosphonopeptides n-terminaux consiste à utiliser la chaine peptidique chirale pour induire une asymétrie sur le carbone directement lié au phosphore. Le couplage peptidique a également été mis au point entre l'acide phosphonoacetique et l'acide 6-aminopenicillanique dans le but de préparer de nouveaux antibiotiques. L'étude du comportement des phosphonopeptides n-terminaux en tant que réactifs de Honer a été abordée pour préparer des peptides insaturés, substituts possibles de peptides à usage thérapeutique. Enfin, la réactivité de thiols sur les chlorures d'acides 2-dialkylphosphonoalcanoiques constitue une voie de synthèse de dialcoxyphosphorylalcane thioates de s-alkyle, qui conduisent eux-mêmes par réaction de Horner à des thioesters éthyléniques, cette réaction des généralisable aux dérivés chrysanthemiques
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Louaisil, Nicolas. "Synthèse asymétrique d'acides α-aminophosphoniques hétérocycliques d'intérêts biologiques." Paris 11, 2008. http://www.theses.fr/2008PA112166.

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Ce mémoire est consacré à la synthèse d’acides α-aminophosphoniques hétérocycliques à 6 chaînons potentiellement bioactifs. Cette synthèse repose sur l’addition hautement stéréosélective d’un phosphite nucleophile sur des ions iminiums issus de cétones hétérocycliques. La première partie, expose la synthèse d’acides α-aminophosphoniques hétérocyclohexaniques dans lesquels l’hétéroélément (oxygène, soufre et azote) est en position-4 ou en position-3 par rapport à la fonction acide phosphonique. Les aminophosphonates sont obtenus avec de bons rendements par une réaction «one-pot» à partir de cétones hétérocycliques, d’amines et de phosphites, et sont ensuite transformés en acides phosphoniques hétérocyclohexaniques racémiques ou énantiopurs dont la plupart sont jusqu’alors inconnus. La seconde partie, détaille la première synthèse d’acides α-aminophosphoniques β-hydroxylés hétérocycliques, préparés en six étapes à partir de cétones hétérocycliques. La synthèse du précurseur diaminé racémique d’analogues phosphorés d’une famille d’agents antiarythmiques est aussi décrite. Cette partie rapporte également la synthèse des acides α- aminophosphoniques β-hydroxylés énantiopurs (X = S, O, NR), dont l’étape clé, formant simultanément deux centres stéréogènes, est une réaction stéréosélective d’addition du phosphite sur des imines bicycliques. Celles-ci sont préparées par une réaction « one-pot », impliquant trois étapes à partir d’acétals portant une copule chirale. Les aminophosphonates hétérobicycliques ainsi obtenus avec une excellente diastéréosélectivité donnent après traitement les acides α-amino-β-hydroxy-phosphoniques hétérocycliques
Heterocyclic α-Aminophosphonic acids are currently of great interest as potential bioactive compounds. In this work the key-step of these synthesis is based on a highly stéréosélective addition of phosphite to iminium ions formed from heterocyclic ketones. Firstly, we report the synthesis new of heterocyclic α-aminophosphonic acids bearing oxygen, nitrogen or sulfur as the heteroatom in positions three or four relative to the phosphonic acid moiety. This is achieved via a one-pot reaction between a heterocyclic ketone, amine and phosphite to form the key aminophosphonate intermediate. Subsequent amino deprotection and acid hydrolysis yielded the final heterocyclic α-aminophosphonic acids in racemic and enantiopure form. Secondly, the first synthesis of heterocyclic α-amino-β-hydroxyphosphonic acids is reported in six steps from the heterocyclic ketone, including an optically active β-hydroxy-α-aminophosphonic acid analogue of serine. The key step in this sequence was a stereoselective addition reaction between a phosphite and bicyclic imine to simultaneously generate two new stereogenic centers. The bicyclic imines were prepared from acetals bearing a chiral auxiliary via a one-pot sequence of deprotection, deacetalisation and intramolecular condensation sequence in one-pot. The heterocyclic aminophosphonates were obtained with excellent diastereoselectivity which upon subsequent oxidation and hydrolysis yielded optically active α-aminophosphonic acids. The absolute configurations of some compounds were determined by X-ray crystallography
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Martel, Sophie. "Les aminophosphonates : des marqueurs de pH en RMN du 31P : de l'étude physico-chimique à la biologie." Aix-Marseille 1, 2002. http://www.theses.fr/2002AIX11042.

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Pour fournir des sondes capables de mesurer les gradients de pH cellulaires par RMN du 31P, et d'atteindre les compartiments acides des cellules, nous avons préparé 27 amines phosphorées (dont 13 nouvelles). Outre une large gamme de pKa (1 à 7), ces marqueurs présentent une grande sensibilité "DELTAdelta" (différence de déplacement chimique entre les formes acides "delta"a et basique "delta"b), et ont l'avantage de résonner loin des autres métabolites phosphorés. Dans ce travail, nous avons déterminé les facteurs influençant la valeur du pKa, des "delta"a et des "delta"b de ces composés. Nous avons démontré que le pKa peut être corrélé aux effets inductifs de ("sigma"u) des substituants entourant la fonction amine et à l'effet stérique (Es) du plus encombrant de ces substituants. De la même façon, "delta"a et "delta"b ont été corrélés aux "sigma"u et aux angles de pyramidalisation (α) du 31P obtenus par modélisation moléculaire. Il a également été montré que la large sensibilité des aminophosphonates par rapport aux autres marqueurs (Pi ou phosphates), pouvait être due à la large différence d'angle entre les deux formes extrêmes. Tout ceci a permis la mise au point d'une relation empirique simple où les valeurs pKa "delta"a et "delta"b sont corrélées directement à la structure des amines. Les temps de relaxation du 31P(T1) et les largeurs de raie du signal RMN (W) ont également été mesurés et nous avons entrepris de déterminer les facteurs influençant ces paramètres. Des études dans différents milieux biologiques ont montré que la pKa, les "delta"a, les "delta"b et les T1 des aminophosphonates sont peu sensibles à la force ionique et aux molécules présentes dans ces milieux, rendant ces composés utilisables en vivo. Ainsi, un des marqueurs, la DEPMPH, a permis la première détection directe par RMN du 31P des compartiments acides et le suivi des variations de pH pendant l'ischémie et la reperfusion du foie de rat isolé , et de mesurer directement le pH intra- et extracellulaire dans le cœur de rat isolé lors d'un protocole d'ischémie/reperfusion.
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Kaur, T. "Synthesis of antibacterial natural products: primin, centrolobine, oenostacin and studies on the synthesis of alpha-aminophosphonates and metallopnas." Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 2013. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/2180.

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Book chapters on the topic "Aminophosphonates"

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Song, Baoan, Linhong Jin, Song Yang, and Pinaki S. Bhadury. "Studies on α-Aminophosphonates with Antiviral Activity." In Environment-Friendly Antiviral Agents for Plants, 7–93. Berlin, Heidelberg: Springer Berlin Heidelberg, 2010. http://dx.doi.org/10.1007/978-3-642-03692-7_2.

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Dake, Satish A. "Environmentally Friendly Approach: Synthesis and Biological Evaluation of α-Aminophosphonate Derivatives." In Green Chemistry and Sustainable Technology, 95–136. Includes bibliographical references and index.: Apple Academic Press, 2020. http://dx.doi.org/10.1201/9780367808310-5.

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Ammann, Adrian A. "Speciation of Aminopolycarboxylate and Aminophosphonate Metal Complexes by AEX ICP-MS in Environmental Water Samples." In Biogeochemistry of Chelating Agents, 108–20. Washington, DC: American Chemical Society, 2005. http://dx.doi.org/10.1021/bk-2005-0910.ch005.

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"6. Synthesis of α-aminophosphonates by the Kabachnik–Fields reaction and by the Pudovik reaction." In Organophosphorus Chemistry, 108–47. De Gruyter, 2018. http://dx.doi.org/10.1515/9783110535839-006.

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Hassner, A., and I. Namboothiri. "KABACHNIK–FIELD Aminophosphonate Synthesis to KURSANOV–PARNES Ionic Hydrogenation." In Organic Syntheses Based on Name Reactions, 245–78. Elsevier, 2012. http://dx.doi.org/10.1016/b978-0-08-096630-4.01115-6.

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Conference papers on the topic "Aminophosphonates"

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Shakurova, E. R., and L. V. Parfenova. "Three-component synthesis of aminophosphonates based on phenylenediamines." In ACTUAL PROBLEMS OF ORGANIC CHEMISTRY AND BIOTECHNOLOGY (OCBT2020): Proceedings of the International Scientific Conference. AIP Publishing, 2022. http://dx.doi.org/10.1063/5.0069157.

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Santhisudha, S., G. Mohan, C. Sridevi, N. Bakthavatchala Reddy, Grigory V. Zyryanov, and C. Suresh Reddy. "Calcium bromide catalysed synthesis and anticoagulant activity of bis(α-aminophosphonates)." In PROCEEDINGS OF INTERNATIONAL CONFERENCE ON RECENT TRENDS IN MECHANICAL AND MATERIALS ENGINEERING: ICRTMME 2019. AIP Publishing, 2020. http://dx.doi.org/10.1063/5.0018177.

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Keglevich, György, and Erika Bálint. "Synthesis of α-aminophosphonates and related derivatives under microwave conditions." In The 21st International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2017. http://dx.doi.org/10.3390/ecsoc-21-04716.

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Mudila, Harish, Himanshu Kapoor, and Parteek Prasher. "One pot green synthesis of α-aminophosphonates with D-Malic acid as an organocatalyst." In RECENT ADVANCES IN FUNDAMENTAL AND APPLIED SCIENCES: RAFAS2016. Author(s), 2017. http://dx.doi.org/10.1063/1.4990356.

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Gütschow, Michael, and Daniela Häußler. "Aminophosphonates as Novel Activity-Based Probes for Matriptase-2 ." In 1st International Electronic Conference on Medicinal Chemistry. Basel, Switzerland: MDPI, 2015. http://dx.doi.org/10.3390/ecmc-1-a041.

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Ali, Tarik, Salah Abdel-Aziz, Somaya El-Edfawy, El-Hossain Mohamed, and Somaia Abdel-Kariem. "Cleavage of Diethyl Chromonyl α-Aminophosphonate with Nitrogen and Carbon Nucleophiles: A Synthetic Approach and Biological Evaluations of A Series of Novel Azoles, Azines and Azepines Containing α-Aminophosphonate and Phosphonate Groups." In The 18th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2014. http://dx.doi.org/10.3390/ecsoc-18-a013.

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