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Journal articles on the topic 'Aminophosphonates'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 September 2023

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1

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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2

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

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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11

Shashikumar, Nellisara D. "Preparation of Newα-Aminophosphonate Derivatives by Kabachnik-Fields Reaction Using a Recyclable Catalyst." Journal of Chemistry 2013 (2013): 1–8. http://dx.doi.org/10.1155/2013/240381.

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A convenient and efficient synthetic method for the preparation of some newα-aminophosphonate derivatives via a one-pot three-component system has been achieved using Amberlite IRC-748 as a recyclable catalyst. This method not only provides an excellent complement for the synthesis ofα-aminophosphonates but also avoids the use of hazardous acids or expensive/toxic Lewis acids and harsh reaction conditions. Most of the synthesized compounds (4a–o) exhibited activity against bacteria/fungi strains and moderate DPPH radical scavenging activity.

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12

López-Francés, Adrián, Xabier del Corte, Edorta Martínez de Marigorta, Francisco Palacios, and Javier Vicario. "Ugi Reaction on α-Phosphorated Ketimines for the Synthesis of Tetrasubstituted α-Aminophosphonates and Their Applications as Antiproliferative Agents." Molecules 26, no. 6 (March 16, 2021): 1654. http://dx.doi.org/10.3390/molecules26061654.

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An Ugi three-component reaction using preformed α-phosphorated N-tosyl ketimines with different isocyanides in the presence of a carboxylic acid affords tetrasubstituted α-aminophosphonates. Due to the high steric hindrance, the expected acylated amines undergo a spontaneous elimination of the acyl group. The reaction is applicable to α-aryl ketimines bearing a number of substituents and several isocyanides. In addition, the densely substituted α-aminophosphonate substrates showed in vitro cytotoxicity, inhibiting the growth of carcinoma human tumor cell line A549 (carcinomic human alveolar basal epithelial cell).

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13

Nassan, Mohamed A., Adil Aldhahrani, Hamada H. Amer, Ahmed Elhenawy, Ayman A. Swelum, Omar M. Ali, and Yasser H. Zaki. "Investigation of the Anticancer Effect of α-Aminophosphonates and Arylidine Derivatives of 3-Acetyl-1-aminoquinolin-2(1H)-one on the DMBA Model of Breast Cancer in Albino Rats with In Silico Prediction of Their Thymidylate Synthase Inhibitory Effect." Molecules 27, no. 3 (January 24, 2022): 756. http://dx.doi.org/10.3390/molecules27030756.

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Breast cancer is a major cause of death in women worldwide. In this study, 60 female rats were classified into 6 groups; negative control, α-aminophosphonates, arylidine derivatives of 3-acetyl-1-aminoquinolin-2(1H)-one, DMBA, DMBA & α-aminophosphonates, and DMBA & arylidine derivatives of 3-acetyl-1-aminoquinolin-2(1H)-one. New α-aminophosphonates and arylidine derivatives of 3-acetyl-1-aminoquinolin-2(1H)-one were synthesized and elucidated by different spectroscopic and elemental analysis. Histopathological examination showed marked proliferation of cancer cells in the DMBA group. Treatment with α-aminophosphonates mainly decreased tumor mass. Bcl2 expression increased in DMBA-administered rats and then declined in the treated groups, mostly with α-aminophosphonates. The level of CA15-3 markedly declined in DMBA groups treated with α-aminophosphonates and arylidine derivatives of 3-acetyl-1-aminoquinolin-2(1H)-one. Gene expression of GST-P, PCNA, PDK, and PIK3CA decreased in the DMBA group treated with α-aminophosphonates and arylidine derivatives of 3-acetyl-1-aminoquinolin-2(1H)-one, whereas PIK3R1 and BAX increased in the DMBA group treated with α-aminophosphonates and arylidine derivatives of 3-acetyl-1-aminoquinolin-2(1H)-one. The molecular docking postulated that the investigated compounds can inhibt the Thymidylate synthase TM due to high hydrophobicity charachter.

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14

Wavhal, Kamalakar Kailash, and Deepak Manik Nagrik. "Synthesis of Biologically Potent α-Aminophosphonates Derivatives by Nano-Catalyst." Oriental Journal Of Chemistry 38, no. 5 (October 31, 2022): 1314–19. http://dx.doi.org/10.13005/ojc/380532.

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α-Aminophosphonate and their derivatives are biologically potent and have received considerable attention in a recent research scenario. The main reason is that they show triguing biological activity. α-Aminophosphonate derivatives are gaining a lot of importance in medicinal chemistry due to their application as enzyme inhibitors, herbicides, antibiotics, pharmaceutical agents and inhibitors of Excitatory Post-Synaptic Potential(EPSP) synthesis, and HIV Protease. It is also important in ati-cancer, anti-HIV, antithrombotic and antibacterial, antioxidant activity. Unfortunately, these compounds have certain limitation such as extraction, purification, of bioactive molecule and their minimum yields. For this reason, many scientists have been orienting their research towards the synthesis of molecules as a new tool to overcome this problems he prime focus of this work is the combination of three reactant derivative of benzaldehyde derivative of aniline, and diethyl phosphonate to form α-aminophosphonates derivatives by multicomponent reaction(KFR). The novel nano-catalyst i.e. polyanilinedoped with manganese (PAni-Mn) was prepared. The catalyst shows excellent catalytic activity, high yields, short reaction times, easy synthesis. The PAni was fully characterized by X-ray diffraction, TEM, SEM, and FT-IR technique.

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15

Elharony, Noura Elsayed, Ibrahim El Tantawy El Sayed, Abdullah G. Al-Sehemi, Ahmed A. Al-Ghamdi, and Ahmed S. Abou-Elyazed. "Facile Synthesis of Iron-Based MOFs MIL-100(Fe) as Heterogeneous Catalyst in Kabachnick Reaction." Catalysts 11, no. 12 (November 29, 2021): 1451. http://dx.doi.org/10.3390/catal11121451.

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An effective technique was proposed for the synthesis of novel α-aminophosphonates: a three-component one-pot condensation reaction of aniline, aromatic aldehydes, and triphenyl phosphite in the presence of (MIL-100(Fe)) as a heterogeneous catalyst. Initially, MIL-100(Fe) was synthesized using H3BTC and ferric nitrate at low temperature and atmospheric pressure. Further, MIL-100(Fe) was characterized using various techniques such as XRD, BET surface area, scanning electron microscopy (SEM), Fourier-transform infrared (FT-IR), and thermogravimetric analysis (TGA). Herein, MIL-100(Fe) showed exceptional catalytic performance for the synthesis of α-aminophosphonate and its derivatives compared with conventional solid catalysts, and even homogeneous catalysts. The study demonstrated that MIL-100(Fe) is an ecofriendly and easily recyclable heterogeneous catalyst in Kabachnick reactions for α-aminophosphonate synthesis, with high yield (98%) and turnover frequency (TOF ~ 3.60 min−1) at room temperature and a short reaction time (30 min).

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16

Souii, Ichrak, Med Abderrahmane Sanhoury, Javier Vicario, Xabier Jiménez-Aberásturi, Mohamed L. Efrit, Hedi M’rabet, and Jesús M. de los Santos. "Synthesis and Characterization of a New Series of Bis(allylic-α-aminophosphonates) under Mild Reaction Conditions." Molecules 28, no. 12 (June 9, 2023): 4678. http://dx.doi.org/10.3390/molecules28124678.

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Several bis(α-aminophosphonates) have been conveniently prepared in good yields using a straightforward multicomponent Kabachnik–Fields reaction between ethane 1,2-diamine or propane 1,3-diamine, diethylphosphite and aldehydes under catalyst-free conditions. The nucleophilic substitution reaction of bis(α-aminophosphonates) prepared and ethyl (2-bromomethyl)acrylate under mild reaction conditions afforded an original synthetic approach to a new series of bis(allylic-α-aminophosphonates).

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17

Cai, Yan, Yuming Li, Minxuan Zhang, Jiaxin Fu, and Zhiwei Miao. "Regioselective BF3·Et2O-catalyzed C–H functionalization of indoles and pyrrole with reaction of α-diazophosphonates." RSC Advances 6, no. 73 (2016): 69352–56. http://dx.doi.org/10.1039/c6ra15329a.

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A regioselective synthesis of β-(3-indol)-β-aminophosphonates and β-(2-pyrrol)-β-aminophosphonates was developed through an intermolecular C–H insertion of α-diazophosphonates with indole and pyrrole derivatives catalyzed by BF₃·Et₂O.

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18

Yuan, Jin-Wei, and Wei-Jie Li. "Mg(OCH3)2-mediated one-pot synthesis of α-aminophosphonate derivatives of cytosine under mild conditions." Zeitschrift für Naturforschung B 72, no. 8 (August 28, 2017): 563–71. http://dx.doi.org/10.1515/znb-2017-0044.

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AbstractAn efficient one-pot synthesis of α-aminophosphonates of cytosine with aldehydes, diisopropyl H-phosphite, and cytosine with the help of simple magnesium methanolate was discovered. α-Aminophosphonates of cytosine were obtained in good yields under mild conditions. The reaction tolerates both electron-donating and electron-withdrawing substituents of aromatic and aliphatic aldehydes.

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19

Trela, Zenon, Halina Kleszczyńska, and Janusz Sarapuk. "Physiological and Hemolytic Toxicity of Some Aminophosphonates." Zeitschrift für Naturforschung C 56, no. 9-10 (October 1, 2001): 838–42. http://dx.doi.org/10.1515/znc-2001-9-1026.

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AbstractThe effect of novel synthesized aminophosphonates on membrane potential and electrical conductance of internodal cells of Nitellopsis obtusa and hemolysis of erythrocytes (RBC) was studied. It was found that those the organophosphorous compounds, when present at 10-100 μm concentrations, caused depolarization and increased electrical conductance of alga membranes. They also influenced fluidity of erythrocyte membranes. When used at higher concentrations aminophosphonates caused hemolysis of RBC. The changes observed depended on structural features of the aminophosphonates, i.e., substituents at the carbon, phosphorus and nitrogen atoms, and, most probably, may be the result of direct interaction of the am inophosphonates with the lipid phase of the plasma membrane and the induced structural changes. Two modes of interaction are proposed.

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20

Reddy, Gajjala Raghavendra, Chinta Raveendra Reddy, Gopireddy Venkata Subba Reddy, Pasupuleti Visweswara Rao, Meenakshisundaram Swaminathan, Balam Satheeh Krishna, and Cirandur Suresh Reddy. "Synthesis of New 4-Chloro-6-Methylpyrimidin-2-yl-Aminophosphonates as Potential DU145 and A549 Cancer Cell Inhibitors." Letters in Drug Design & Discovery 17, no. 4 (April 25, 2020): 396–410. http://dx.doi.org/10.2174/1570180816666190329223207.

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: A series of new α-aminophosphonates containing potential anticancer active 4-chloro-6- methylpyrimidin-2-amino pharmacophore were synthesized. Background: α-Aminophosphonates are of growing interest to the researchers due to their biological activities. Besides aminophosphoryl functionality, which is responsible for the vital activity, incorporation of a captivating pharmacophore on it will definitely enrich its activity. Objective: Erstwhile many of the reported α-aminophosphonates impregnated with bioactive heterocycles like quinazoline, chromene, pyrazole, furan and thiophene were used as anticancer drugs, and we are intended to enhance the anticancer potentiality of α-aminophosphonates by substituting a new 4-chloro-6-methylpyrimidin-2-yl group into its structure, specifically on nitrogen atom. Methods: Title compounds were synthesized by Kabachnik-Fields reaction by using sulfated Titania, a solid acid catalyst that is encompassed with high density of Lewis acidic reaction sites. The series of synthesized compounds were screened for in vitro anti-cancer activity and their ADMET, QSAR and drug properties studied. Results: Structures of all the title compounds synthesized in high yields were confirmed by spectral & elemental analyses. Their anti-cancer screening studies on various cell lines and evaluation of other properties revealed their potentiality towards the inhibition of growth of DU145 & A549 cell lines. Conclusion: The substitution of 4-chloro-6-methylpyrimidin-2-amino moiety on to the amino functionality of the α-aminophosphonates is a critical task invariably due to the substitutions that are located on α-carbon. As such, this substitution had increased the scope for growth inhibition of DU145 and A549 cancer cells.

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21

Varga, Petra R., and György Keglevich. "The Last Decade of Optically Active α-Aminophosphonates." Molecules 28, no. 16 (August 20, 2023): 6150. http://dx.doi.org/10.3390/molecules28166150.

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α-Aminophosphonates and related compounds are important due to their real and potential biological activity. α-Aminophosphonates may be prepared by the Kabachnik–Fields condensation of oxo compounds, amines and dialkyl phosphites, or by the aza-Pudovik addition of the same P-reagents to imines. In this review, the methods that allow for the synthesis of α-aminophosphonates with optical activity are surveyed. On the one hand, optically active catalysts or ligands may induce enantioselectivity during the Kabachnik–Fields reaction. On the other hand, asymmetric catalysis during the aza-Pudovik reaction, or hydrogenations of iminophosphonates, may prove to be a useful tool. Lastly yet importantly, it is possible to start from optically active reagents that may be associated with diastereoselectivity. The “green” aspects of the different syntheses are also considered.

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22

Rezaei, Zahra, Soghra Khabnadideh, Kamiar Zomorodian, Keyvan Pakshir, Setareh Nadali, Nadia Mohtashami, and Ehsan Faghih Mirzaei. "Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates." International Journal of Medicinal Chemistry 2011 (September 26, 2011): 1–11. http://dx.doi.org/10.1155/2011/678101.

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α-Aminophosphonates are bioisosteres of amino acids and have several pharmacological activities. These compounds have been synthesized by various routes from reaction between amine, aldehyde, and phosphite compounds. In order to synthesize α-aminophosphonates, catalytic effect of CuCl2 was compared with FeCl3. Also all designed structures as well as griseofulvin were docked into the active site of microtubule (1JFF), using Autodock program. The results showed that the reactions were carried out in the presence of CuCl2 in lower yields, and also the time of reaction was longer in comparison with FeCl3. The chemical structures of the new compounds were confirmed by spectral analyses. The compounds were investigated for antifungal activity against several fungi in comparison with griseofulvin. An indole-derived bis(α-aminophosphonates) with the best negative ΔG in docking study showed maximum antifungal activity against Microsporum canis, and other investigated compounds did not have a good antifungal activity.

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23

Bálint, Erika, Ádám Tajti, Anna Ádám, István Csontos, Konstantin Karaghiosoff, Mátyás Czugler, Péter Ábrányi-Balogh, and György Keglevich. "The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction." Beilstein Journal of Organic Chemistry 13 (January 12, 2017): 76–86. http://dx.doi.org/10.3762/bjoc.13.10.

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A family of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reactivity was mapped, and the fine mechanism was evaluated by DFT calculations. Two α-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N–H···O=P intermolecular hydrogen bridges pair.

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24

Peng, Yungui, Yanqiang Ning, Songlin Tan, Dezhong Li, and Na Liao. "Sulfonyl as a Traceless Activation Group for Enantioselective Mannich Reaction Catalyzed by Thiourea to Access Chiral β-Aminophosphonates." Synlett 29, no. 05 (January 19, 2018): 678–82. http://dx.doi.org/10.1055/s-0036-1589156.

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An efficient enantioselective Mannich reaction of N-protected α-sulfones with β-benzenesulfonyl phosphonates was developed by using a chiral cinchona alkaloid-derived thiourea as a catalyst. This method was used to obtain a series of chiral α-sulfonyl-β-aminophosphonates in yields of up to 96% with 89:11 dr and 88% ee. These compounds were further transformed into β-aminophosphonates or chiral azetidines with various functional groups by a Horner–Wadsworth–Emmons/aza-Michael addition reaction sequence.

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Sobhani, Sara, Elham Safaei, Mozaffar Asadi, Fariba Jalili, and Zahra Tashrifi. "Efficient synthesis of secondary and primary dialkyl α-aminophosphonates catalyzed by tetramethyl-tetra-3,4-pyridinoporphyrazinato copper(II) methyl sulfate under solvent-free conditions." Journal of Porphyrins and Phthalocyanines 12, no. 07 (July 2008): 849–56. http://dx.doi.org/10.1142/s1088424608000248.

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An efficient method for the synthesis of secondary and primary dialkyl α-aminophosphonates under solvent-free conditions by one-pot reaction of aldehydes/ketones, amines/ammonium acetate and trialkyl/diethyl phosphite in the presence of a low catalytic amount of [ Cu (3,4-tmtppa)]( MeSO 4)4(0.16 mol%) as a highly stable and reusable catalyst, is described. By this method, aromatic, aliphatic, cyclic and heterocyclic aldehydes, hindered and cage ketones are converted into their corresponding α-aminophosphonates in good to excellent yields.

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Bálint, Erika, Ádám Tajti, Katalin Ladányi-Pára, Nóra Tóth, Béla Mátravölgyi, and György Keglevich. "Continuous flow synthesis of α-aryl-α-aminophosphonates." Pure and Applied Chemistry 91, no. 1 (January 28, 2019): 67–76. http://dx.doi.org/10.1515/pac-2018-0923.

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AbstractThe synthesis of α-aryl-α-aminophosphonates was performed by the three-component Kabachnik-Fields reaction of primary amines, benzaldehyde derivatives and dialkyl phosphites in a continuous flow microwave reactor. The target compounds could be obtained in high (~90%) yields without any catalyst in simple alcohols as the solvent. The flow process elaborated required shorter reaction times and lower excess of the reagent, as compared to the “traditional” batch reactions, and allowed the synthesis of the α-aminophosphonates on a somewhat larger scale.

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27

Rogacz, Diana, Jarosław Lewkowski, Marta Siedlarek, Rafał Karpowicz, Anna Kowalczyk, and Piotr Rychter. "The Effect of New Thiophene-Derived Diphenyl Aminophosphonates on Growth of Terrestrial Plants." Materials 12, no. 12 (June 24, 2019): 2018. http://dx.doi.org/10.3390/ma12122018.

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The aim of this work was to evaluate the impact of the thiophene-derived aminophosphonates 1–6 on seedling emergence and growth of monocotyledonous oat (Avena sativa) and dicotyledonous radish (Raphanus sativus L.), and phytotoxicity against three persistent and resistant weeds (Galinsoga parviflora Cav., Rumex acetosa L., and Chenopodium album). Aminophosphonates 1–6 have never been described in the literature. The phytotoxicity of tested aminophosphonates toward their potential application as soil-applied herbicides was evaluated according to the OECD (Organization for Economic and Cooperation Development Publishing) 208 Guideline. In addition, their ecotoxicological impact on crustaceans Heterocypris incongruens and bacteria Aliivibrio fischeri was measured using the OSTRACODTOXKITTM and Microtox® tests. Obtained results showed that none of the tested compounds were found sufficiently phytotoxic and none of them have any herbicidal potential. None of the tested compounds showed important toxicity against Aliivibrio fischeri but they should be considered as slightly harmful. Harmful impacts of compounds 1–6 on Heterocypris incongruens were found to be significant.

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Salgado-Escobar, Oscar, Alexis Hernández-Guadarrama, Ivan Romero-Estudillo, and Irma Linzaga-Elizalde. "Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines." Molecules 24, no. 2 (January 15, 2019): 294. http://dx.doi.org/10.3390/molecules24020294.

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A straightforward and novel method for transformation of readily available 1,3-benzoxazines to secondary phosphonates and α-aminophosphonates using boron trifluoride etherate as catalyst is developed. The formation of phosphonates proceeds through ortho-quinone methide (o-QM) generated in situ, followed by a phospha-Michael addition reaction. On the other hand, the α-aminophosphonates were obtained by iminium ion formation and the subsequence nucleophilic substitution of alkylphosphites. This method can be also used for the preparation of o-hydroxybenzyl ethers through oxa-Michael addition.

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29

Zhou, Liang. "Synthesis and Characterization of Aminophosphonates Zirconium as New Mesoporous Materials." E-Journal of Chemistry 9, no. 3 (2012): 1320–26. http://dx.doi.org/10.1155/2012/640317.

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A serial of aminophosphonates zirconium with the different arm lengths of –(CH2)n– organic chains (n=2–6) was synthesized for the first time. These compounds are characterized by FT-IR, SEM, TEM, TG and nitrogen adsorption-desorption. And based on the experimental data, these materials not only have layer structure mesoporous and good thermal stability such as zirconium phosphate, but also can be adjusted the layer distance, pore size and pore volume. So aminophosphonates zirconium posses special excellent properties and will have potential prospect applications.

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30

Nikitin, Evgeny, Georgy Shumatbaev, Dmitriy Terenzhev, Kirill Sinyashin, and Kamila Kazimova. "New α-Aminophosphonates as Corrosion Inhibitors for Oil and Gas Pipelines Protection." Civil Engineering Journal 5, no. 4 (April 27, 2019): 963–70. http://dx.doi.org/10.28991/cej-2019-03091303.

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The problem of corrosion of metal equipment is one of the most actual problems in oil industry. One of the methods to solve this problem is the development of new low-toxic, accessible and effective corrosion inhibitors. For this purpose, we carried out the synthesis of the new α-aminophosphonates based on syntanyl phosphites, formalin and diethanolamine according to the Kabachnik-Fields reaction. The resulting products are characterized by 1H, 31P, 13C NMR, IR and mass spectroscopy methods. The obtained compounds contain a long radical chain of industrial (poly)ethoxylated alcohol residue with different length of the hydroxyethyl fragment, as well as an active center containing O-P-C-N fragment, which impart them inhibitory properties toward corrosion processes. The anticorrosive activity of the new aminophosphonates was studied by gravimetric analysis method. In the article the effect of concentration, time and degree of ethoxylation of the hydrocarbon radical in alpha-aminophosphonates on the protective effect of inhibitors was studies. It was shown that the obtained aminophosphonates exhibit high values of the protective effect of steel in a highly mineralized medium containing 250 g/m3 СО2 and 200 g/m3 Н2S. The high value of the protective effect (82-85 %) at inhibitor concentration of 25 mg/l was found. The maximum protective effect at 50 mg/ml dosage of the inhibitor is 94.3 %, while there is a decrease of the corrosion rate (less than 0.04 mm/year).

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Maestro, Aitor, Xabier del Corte, Adrián López-Francés, Edorta Martínez de Marigorta, Francisco Palacios, and Javier Vicario. "Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives." Molecules 26, no. 11 (May 27, 2021): 3202. http://dx.doi.org/10.3390/molecules26113202.

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Due to their structural similarity with natural α-amino acids, α-aminophosphonic acid derivatives are known biologically active molecules. In view of the relevance of tetrasubstituted carbons in nature and medicine and the strong dependence of the biological activity of chiral molecules into their absolute configuration, the synthesis of α-aminophosphonates bearing tetrasubstituted carbons in an asymmetric fashion has grown in interest in the past few decades. In the following lines, the existing literatures for the synthesis of optically active tetrasubstituted α-aminophosphonates are summarized, comprising diastereoselective and enantioselective approaches.

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32

Lewkowski, Jarosław, Edyta Rzeszotarska, Agnieszka Matusiak, Marta Morawska, Gabriela Gajek, Karolina Nowak, and Renata Kontek. "Cytotoxic Action of N-aryl, Furan-derived Aminophosphonates against HT29 and HCT116 Cancer Cell Lines." Anti-Cancer Agents in Medicinal Chemistry 19, no. 4 (June 25, 2019): 453–62. http://dx.doi.org/10.2174/1871520619666181122115649.

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Background: The anticancer activity of aminophosphonic derivatives has been described extensively, some recent papers included furan-derived aminophosphonates and their cytostatic action against various cancer cells. Objective: A series of twelve furan-derived dibenzyl and diphenyl aminophosphonates 2a-f and 3a-f was synthesized and tested in aspect of their cytotoxic action on two cell lines of colorectal cancer: HT29 and HCT116. Seven of them are new compounds, while the rest five have already been published by us, together with their cytotoxic action against squamous esophageal cancer cells. Methods: To estimate the cytotoxicity effect of tested compounds MTT test was used. Pro-apoptotic activity of five selected compounds was evaluated using APC Annexin V Apoptosis Detection Kit on a flow cytometer. Quantification of caspases 3/7 activity was performed using Caspase-Glo® 3/7 Assay Kit. Results: Five of these aminophosphonates showed significant cytotoxicity higher than those of cisplatin. Simultaneous evaluation of their cytotoxicity against PBLs revealed that these compounds are rather not harmful for regular human lymphocytes. Tests on apoptosis vs. their necrotic actions on cells were performed with selected compounds showing the most significant cytotoxicity against cancer cells and all tested compounds did not induce significant increase of necrosis in cells, whereas they showed moderate-to-strong proapoptotic actions even at the lowest applied concentration. Caspase 3/7 activity results confirmed proapoptotic properties of tested aminophosphonates. Conclusion: From among studied compounds, dibenzyl N-phenyl substituted amino(2-furyl)methylphsophonates were found to be more potent compounds in aspect of their antiproliferative action than the corresponding diphenyl derivatives.

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33

Kowalczyk, Dorota, and Łukasz Albrecht. "An organocatalytic biomimetic approach to α-aminophosphonates." Chemical Communications 51, no. 19 (2015): 3981–84. http://dx.doi.org/10.1039/c4cc09477h.

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34

Lewkowski, J., R. Karpowicz, M. Morawska, P. Rychter, D. Rogacz, K. Lewicka, and P. Dobrzyński. "Synthesis and ecotoxicological impact of ferrocene-derived amino-phosphonates using a battery of bioassays." RSC Advances 7, no. 61 (2017): 38399–409. http://dx.doi.org/10.1039/c7ra06079c.

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35

Bhagat, Srikant, Parth Shah, Sanjeev K. Garg, Shweta Mishra, Preet Kamal Kaur, Sushma Singh, and Asit K. Chakraborti. "α-Aminophosphonates as novel anti-leishmanial chemotypes: synthesis, biological evaluation, and CoMFA studies." Med. Chem. Commun. 5, no. 5 (2014): 665–70. http://dx.doi.org/10.1039/c3md00388d.

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36

Mao, Liu-Liang, Chen-Chen Li, Qiang Yang, Ming-Xing Cheng, and Shang-Dong Yang. "One-pot synthesis of α-aminophosphonates via a cascade sequence of allylamine isomerization/hydrophosphonylation." Chemical Communications 53, no. 32 (2017): 4473–76. http://dx.doi.org/10.1039/c7cc01391d.

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37

Yan, Zhong, Bo Wu, Xiang Gao, and Yong-Gui Zhou. "Enantioselective synthesis of quaternary α-aminophosphonates by Pd-catalyzed arylation of cyclic α-ketiminophosphonates with arylboronic acids." Chemical Communications 52, no. 72 (2016): 10882–85. http://dx.doi.org/10.1039/c6cc04096a.

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38

Niu, Linbin, Shengchun Wang, Jiamei Liu, Hong Yi, Xing-An Liang, Tianyi Liu, and Aiwen Lei. "Visible light-mediated oxidative C(sp3)–H phosphonylation for α-aminophosphonates under oxidant-free conditions." Chemical Communications 54, no. 13 (2018): 1659–62. http://dx.doi.org/10.1039/c7cc09624k.

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39

Oussaid, Adyl, Fatima Benyaqad, Boualem Oussaid, Christian Pradel, and Bernard Garrigues. "Mécanismes de Formation d'α-Aminophosphonates." Phosphorus, Sulfur, and Silicon and the Related Elements 178, no. 6 (June 2003): 1183–97. http://dx.doi.org/10.1080/10426500307903.

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40

Lejczak, Barbara, Pawel Kafarski, and Jan Zygmunt. "Inhibition of aminopeptidases by aminophosphonates." Biochemistry 28, no. 8 (April 1989): 3549–55. http://dx.doi.org/10.1021/bi00434a060.

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41

Palacios, Francisco, Concepción Alonso, and Jesús M. de los Santos. "Synthesis ofβ-Aminophosphonates and -Phosphinates." Chemical Reviews 105, no. 3 (March 2005): 899–932. http://dx.doi.org/10.1021/cr040672y.

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42

Bielecki, Krzysztof, Anna Dziamska, and Janusz Sarapuk. "Physiological Activity of Some Aminophosphonates." Zeitschrift für Naturforschung C 56, no. 11-12 (December 1, 2001): 995–98. http://dx.doi.org/10.1515/znc-2001-11-1215.

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Abstract Influence of some new am inophosphonates on electrolyte leakage from cucumber (Cucu-mis sativus cv "Wisconsin") cotyledons as well as on the content of chlorophyll and activity of guaiacol and pyrogallol peroxidase were studied. Concentration of malondialdehyde (MDA), one of the end-products of lipid peroxidation, was also measured. It was found that am inophosphates influenced the parameters observed to various extents, depending on their structural features and the concentration used. Most active modifiers were those possessing sufficiently long hydrocarbon substituents at the nitrogen atom and/ or iso-propyl chain at the phosphorus atom.

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43

Eyckens, Daniel J., and Luke C. Henderson. "Synthesis of α-aminophosphonates using solvate ionic liquids." RSC Advances 7, no. 45 (2017): 27900–27904. http://dx.doi.org/10.1039/c7ra04407k.

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44

Yamashita, Yasuhiro, Liang Cheng Nam, Mark J. Dutton, Susumu Yoshimoto, and Shū Kobayashi. "Catalytic asymmetric endo-selective [3+2] cycloaddition reactions of Schiff bases of α-aminophosphonates with olefins using chiral metal amides." Chemical Communications 51, no. 96 (2015): 17064–67. http://dx.doi.org/10.1039/c5cc07066j.

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45

Aissa, Rim, Samia Guezane-Lakoud, Emilie Kolodziej, Martial Toffano, and Louisa Aribi-Zouioueche. "Diastereoselective synthesis of bis(α-aminophosphonates) by lipase catalytic promiscuity." New Journal of Chemistry 43, no. 21 (2019): 8153–59. http://dx.doi.org/10.1039/c8nj06235h.

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46

Szewczyk, M. Z., M. Rapp, D. Virieux, J. L. Pirat, and H. Koroniak. "α,α-Difluoro-β-iminophosphonates, an alternative strategy towards the synthesis of α,α-difluoro-β-aminophosphonate derivatives." New Journal of Chemistry 41, no. 14 (2017): 6322–33. http://dx.doi.org/10.1039/c7nj00997f.

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47

da Silva, Caren D. G., Aline R. Oliveira, Mariana P. D. Rocha, Ramesh Katla, Eriton Rodrigo Botero, Érica C. da Silva, and Nelson Luís C. Domingues. "A new, efficient and recyclable [Ce(l-Pro)]2(Oxa) heterogeneous catalyst used in the Kabachnik–Fields reaction." RSC Advances 6, no. 32 (2016): 27213–19. http://dx.doi.org/10.1039/c5ra27064b.

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48

Bhattacharya, Tamalika, Biju Majumdar, Deepa Dey, and Tridib K. Sarma. "Ultrasound mediated synthesis of α-aminophosphonates and 3,4-dihydropyrimidin-2-ones using graphene oxide as a recyclable catalyst under solvent-free conditions." RSC Adv. 4, no. 86 (2014): 45831–37. http://dx.doi.org/10.1039/c4ra08533g.

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Graphene oxide functions as an effective and reusable carbocatalyst for the multicomponent synthesis of α-aminophosphonates and 3,4-dihydropyrimidinones under solvent-free conditions using ultrasonic irradiation.

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49

Aksinenko, A. Yu, and V. B. Sokolov. "Fluorinated α-aminoalkylphosphoryl Compounds. Synthesis, Chemical Properties and Biological Activitiy." Biomedical Chemistry: Research and Methods 1, no. 3 (2018): e00036. http://dx.doi.org/10.18097/bmcrm00036.

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The review reports data on the synthesis of fluorine-containing α-aminophosphonates based on available organophosphorus and fluoroorganic compounds, some of their chemical properties and biological activity.

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50

Ceradini, Davide, and Kirill Shubin. "One-pot synthesis of α-aminophosphonates by yttrium-catalyzed Birum–Oleksyszyn reaction." RSC Advances 11, no. 62 (2021): 39147–52. http://dx.doi.org/10.1039/d1ra07718j.

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