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Sal'keeva, L. K.; Nurmaganbetova, M. T.; Kurmanaliev, O. Sh.; Gazizov, T. Kh.

doi:10.1023/a:1019671324617

Cited by 11 publications

(6 citation statements)

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“…Diisopropyl (Phenyl(phenylamino)methyl)phosphonate (4n) 34 Yield: 82% (285 mg); white solid; mp 103-105 °C (Lit. [34] mp 96 °C). 1 H NMR (250 MHz, CDCl 3 ):  = 0.92 (d, J = 6.1 Hz, 3 H), 1.22 (d, J = 6.2 Hz, 3 H), 1.26 (d, J = 6.2 Hz, 3 H), 1.32 (d, J = 6.2 Hz, 3 H), 4.…”

Section: Diethyl (2-(phenylamino)octan-2-yl)phosphonate (4k)mentioning

confidence: 99%

“…33 Yield: 58% (189 mg); white solid; mp 50-51 °C. Diisopropyl (Phenyl(phenylamino)methyl)phosphonate (4n) 34 Yield: 82% (285 mg); white solid; mp 103-105 °C (Lit. [34] mp 96 °C).…”

Section: Diethyl (2-(phenylamino)octan-2-yl)phosphonate (4k)mentioning

confidence: 99%

“…Diisopropyl(phenyl(phenylamino)methyl)phosphonate (4n)33 White solid (mp: 103-105 °C, Lit: 96°C) (82%, 285 mg)1 H NMR (250 MHz, CDCl 3 ) δ: 0.92 (d, J = 6.1 Hz, 3H), 1.22 (d, J = 6.2 Hz, 3H), 1.26 (d, J = 6.2 Hz, 3H), 1.32 (d, J = 6.2 Hz, 3H), 4.46 (m, 1H), 4.69 (m, 1H), 4.69 (d, J = 15.7 Hz, 1H), 4.69 (Br, 1H), 6.59 (d, J = 7.8 Hz, 2H), 6.68 (t, J = 7.3 Hz, 1H), 7.10 (t, J = 7.8 Hz, 2H), 7.22 -7.36 (m, 3H), 7.43 -7.49 (m, 1H).…”

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An Efficient One-Pot Synthesis of 1-Aminophosphonates

et al. 2022

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1-Aminophosphonates are valuable compounds with wide range applications in biological and industry. Various reaction conditions and catalysts have been reported for the synthesis of 1-aminophosphonates via three components (dialkylphos-phite+aldehyde+amine) or two component reaction (dialkylphos-phite+imine). We report here a solvent-free synthesis of 1-aminophosphonates under very mild reaction condition. Three component condensation reactions of dialkyl phosphite, carbonyl compound, and an amine gave 1-aminophosphonate in good to excellent yield under solvent- and catalyst-free condition at ambient temperature. Hydrophosphorylation of imines in the presence of dialkylphosphite under same condition gave also 1-aminophosphonates in good to excellent yield. These results showed that the reaction needs no to any catalyst or solvent for activation. It seems a tautomeric form of dialkylphosphite (as one of the components) catalysed the reaction. The reaction yield decreased using any solvent. In addition, a novel method will be reported for the synthesis of N-deprotected 1-aminophosphonates (analogues of 1-amino acids) from N-PMP 1-aminophosphonate in the presence of TCCA. To understand the activity of the dialkylphosphite under solvent free condition, the DFT calculations have provided insight into the basis of this activity.

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Section: Diethyl (2-(phenylamino)octan-2-yl)phosphonate (4k)mentioning

confidence: 99%

“…33 Yield: 58% (189 mg); white solid; mp 50-51 °C. Diisopropyl (Phenyl(phenylamino)methyl)phosphonate (4n) 34 Yield: 82% (285 mg); white solid; mp 103-105 °C (Lit. [34] mp 96 °C).…”

Section: Diethyl (2-(phenylamino)octan-2-yl)phosphonate (4k)mentioning

confidence: 99%

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confidence: 99%

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An Efficient One-Pot Synthesis of 1-Aminophosphonates

et al. 2022

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“…During the last decades, it was confirmed that both synthetic and natural α‐aminophosphonates display diverse and useful biological activities [1–3] . For example, they have been used as potential possible pesticide candidates, [4] inhibitors, [5] hypothetical radio protecting agents, [6] antiviral agents, [7] antioxidants, [8] herbicides [9] and plant growth regulators [10] . α‐aminophosphonates have a analogous structure to amino acids and are distinguished by their cell permeability [11] .…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial and Molecular Docking Studies of Novel Synthesized α‐Aminophosphonates Based on Pyrozol Moiety as Anticancer Agents via α‐Topoisomerase II Inhibition

et al. 2023

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The reaction of (1,3-diphenyl-1H-pyrazole-4-carbaldehyde) with different aromatic amines and triethylphosphite in the presence of magnesium perchlorate as a catalyst resulted in high yields of new α-aminophosphonates containing pyrazole moiety. The structures of the newly prepared α-aminophosphonates were confirmed using IR, elemental analysis, 1 H NMR, and 13 C NMR spectra. The antibacterial analysis of the prepared compounds showed potential inhibitory effects against the selected bacterial strains with minimal inhibitory concentrations (MIC) ranging from 12.5 to 3.125 mg/mL compared to the start compound. Some compounds have exhibited higher DPPH scavenging activity. Further, the molecular docking studies illustrated that the synthesized compounds have an inhibitory effect against topoisomerase II, which targets many approved drugs. The best modified α-aminophosphonates compound had the highest binding affinity, with a value of À 7.57 kcal/mol. Modified α-aminophosphonates can be employed as a feasible starting point for generating new antimicrobial and anticancer agents and incorporating new reducing agents into therapeutic formulations.

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“…Different phosphonic derivatives interact with biological systems due to their tetrahedral geometry and the ability to donate or accept protons at physiological pH (Reda et al, 2016). Thus, such structures manifest an inhibiting activity toward aminopeptidases, antiviral (Lejczak et al, 1989;Song et al, 2003;Onita et al, 2010) and antioxidative properties, protectivity toward radiation, and also potential pesticidal features (herbicides or plant growth regulators) (Kleszczyńska et al, 2000;Kleszczyńska and Sarapuk, 2001;Sal'keeva et al, 2002;Sarapuk et al, 2003;Foss et al, 2007). There are many antiviral drugs with phosphonic motives inside the molecules, which are commercially available: e.g., cidofovir, foscarnet, and ganciclovir.…”

Section: Introductionmentioning

confidence: 99%

(S)-Thienyl and (R)-Pirydyl phosphonate Derivatives Synthesized by Stereoselective Resolution of Their Racemic Mixtures With Rhodotorula mucilaginosa (DSM 70403) - Scaling Approaches

et al. 2020

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Rhodotorula mucilaginosa was successfully applied as a biocatalyst for the enantioselective resolution of the racemic mixtures of heteroatom phosphonates derivatives, resulting in receiving the following enantiomers: (S)-1-amino-1(2-thienyl)methylphosphonic acid (Product 1) and (R)-1-amino-1-(3′pirydyl) methylphosphonic acid (Product 2). Biological synthesis of both products is reported for the first time . Pure (S)-1-amino-1-(2-thienyl)methylphosphonic acid (Product 1) was isolated with a conversion degree of 50% after 24 h of biotransformation was conducted on a laboratory scale under moderate conditions (1.55 mM of substrate 1, 100 mL of distilled water, 135 rpm, 25°C; Method A). The scale was enlarged to semi-preparative one, using a simplified flow-reactor (Method C; 3.10 mM of substrate 1) and immobilized biocatalyst. The product was isolated with a conversion degree of 50% just after 4 h of biotransformation. Amino-1-(3′pirydyl)methylphosphonic acid (Substrate 2) was converted according to novel procedure, by the immobilized biocatalyst - Rhodotorula mucilaginosa. The process was carried out under moderate conditions (3.19 mM – substrate 2 solution; Method C1) with the application of a simplified flow reactor system, packed with the yeasts biomass entrapped in 4% agar-agar solution. Pure (R)-amino-1-(3′pirydyl)methylphosphonic (50% of conversion degree) was received within only 48 h.

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Cited by 11 publications

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An Efficient One-Pot Synthesis of 1-Aminophosphonates

An Efficient One-Pot Synthesis of 1-Aminophosphonates

Antimicrobial and Molecular Docking Studies of Novel Synthesized α‐Aminophosphonates Based on Pyrozol Moiety as Anticancer Agents via α‐Topoisomerase II Inhibition

(S)-Thienyl and (R)-Pirydyl phosphonate Derivatives Synthesized by Stereoselective Resolution of Their Racemic Mixtures With Rhodotorula mucilaginosa (DSM 70403) - Scaling Approaches

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