Synthesis and Evaluation of Biological Activity of New Arylphosphoramidates (original) (raw)
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Green synthesis and antimicrobial activities of diphenyl substituted aryl phosphoramidates
Organic communications, 2022
A green, facile and an efficient protocol has been used for the synthesis of new series of diphenyl substituted aryl phosphoramidates by the reaction of diphenyl phosphoryl chloride and various primary/secondary amines using THF as solvent. 1,4-dimethylpiperazine (DMP) was entrenched as a suitable base for catalysing the formation of a P−N linkage. 1 H-NMR, 13 C-NMR, 31 P-NMR and mass spectral studies were used to characterize all the title compounds. The newly synthesized phosphoramidates were screened for their antimicrobial activity. Most of the compounds depicted good to moderate antimicrobial activity when compared to the standard.
Journal of Enzyme Inhibition and Medicinal Chemistry, 2006
Two novel structurally related phosphoramidate compounds, 1 and 2, with likely b-diketone system were synthesized and characterized by 1 H, 13 C, 31 P NMR, IR spectroscopy and elemental analysis. Compound 2 exhibited a 31 P NMR signal which was significantly shielded (8 ppm) relative to compound 1. Determination of human erythrocyte acetylcholinesterase (hAChE) inhibitory activity was carried out according to Ellman's modified kinetic method and the IC 50 values of compounds 1 and 2 were 1.567 and 2.986 mM, respectively. The k i values of 1 and 2 were 1.39 to 2.65 min 21 respectively. A comparison of the bimolecular rate constant (k i) and IC 50 values for the irreversible inhibitors 1 and 2 revealed that the oxono analogue has greater affinity for hAChE than the thiono compound. Furthermore effects of two conventional oximes paralidoxime (A) and obidoxime (B) on reactivation of the inhibited hAChE were studied but low reactivity was shown by both the oximes.
Journal of Enzyme Inhibition and Medicinal Chemistry, 2006
Condensation of 2-hydroxy-1-naphthaldehyde with o-methyl aniline affords the Schiff base, N-(o-methylphenyl)-2-oxo-1-naphthaldimine (HSB). The Schiff base co-ordinates to the nickel(II)-acetate or copper(II)-acetate to give the bis-[N-(o-methylphenyl)-2-oxo-1naphthaldiminato- 2 N,O]nickel(II), [Ni(SB) 2 ] (SB -= deprotonated Schiff base) (1) or bis-[N-(o-methylphenyl)-2-oxo-1-naphthaldiminato- 2 N,O]copper(II), [Cu(SB) 2 ] (2). The Schiff base and complexes are isolated as solids in good yields and characterized by elemental analyses, IR-, UV/Vis.-, 1 H-/ 13 C-NMR-and mass-spectral measurements. 1 H-NMR spectral studies reveal that the complexes are paramagnetic in solution. Reaction with KCN leads to the dissociation of the complexes and provides the free metal atom at zero oxidation state (which is diamagnetic) and anion of the Schiff base (SB -) in the reaction mixture. 1 H-NMR spectra of this reaction mixture confirm the presence of the Schiff base in the complexes (1-2).
Synthesis and insecticidal activity of new phosphoramidates
Compounds known as phosphoramidates have been reported in the literature to have insecticidal activity. In the present investigation, four new phosphoramidates were synthesized and biologically evaluated with regard to their potential insecticidal activity. Moreover, another fifteen compounds had their biological activity profile re-evaluated in further detail against three Lepidoptera species of economic importance. The best results were observed with the four new organophosphates against Ascia monuste.
Phosphorus, Sulfur, and Silicon and the Related Elements, 2013
Series of diphenyl 1-(arylamino)(pyridin-3-yl)methylphosphonates were obtained in high yields from the reactions of nicotinaldehyde with aromatic amines and triphenylphosphite in the presence of titanium tetrachloride as a catalyst. The structures of the synthesized compounds were confirmed by IR, 1 H NMR and mass spectral data and their purities were confirmed by elemental analyses. The synthesized α-aminophosphonates showed moderate to high antimicrobial activities against Escherichia coli (NCIM2065) as a Gramnegative bacterium, Bacillus subtilis (PC1219) and Staphylococcus aureus (ATCC25292) as Gram-positive bacteria and Candida albicans and Saccharomyces cerevisiae as fungi, at various concentrations (10-100 μg/mL). The lethal dose of the synthesized compounds was also determined and indicated that most compounds are safe to use.
Two new categories of a-aminophosphonates molecules were synthesized and characterized by UV-Vis, IR, and NMR. Their spectral properties show a perfect convergence. Their biological activities were evaluated. Molecules 1a, 2a, and 1d present a greater antioxidant potential than BHT and vitamin C. The best anti-inflammatory activity is shown by the 2b molecule and that of 1a, 2a, and 2c molecules are closely comparable to that of diclofenac. The antibacterial activity of the synthesized compounds is significantly higher than the antibiotic amoxicillin. The hemolysis rate HR of compounds 1b, 1c, 2b, and 2c was lower than 5%.