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Synthesis and antimicrobial activity of novel mono- and bis-α-aminophosphonate derivatives

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Abstract

Synthesis of new series of mono and bis α-aminophosphonates in good to excellent yields by one pot three component reaction. The synthesis involved the reaction of carbonyl compounds with amines, triphenyl phosphite at room temperature in dry acetonitrile in presence of lithium perchlorate as Lewis acid catalyst. The chemical structures of the products were characterized by IR, 1HNMR,13CNMR and mass spectral data. All the synthesized compounds were screened for their in vitro antifungal and antibacterial activity against both Gram positive and Gram negative bacterial strains. Compounds 4b, 4d, 5d, 9a showed the highest antibacterial activity against Bacillus subtilis strain with minium inhibition zone 23 mm.

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... An important strategy in fighting antibiotic resistance is the discovery, development of novel antibiotics, and increasing the efficacy of the antibiotic that is already in a clinical study [7]. In this context, α-aminophosphonates gained great interest by medicinal chemists because of their diverse biological and industrial applications such as antibacterial [8][9][10][11][12], anticancer [13][14][15], enzyme inhibitors [16,17], and chelating material [18][19][20][21] which made them a promising drug candidate for further optimization. These compounds are phosphorus analogs of naturally occurring α-amino acids and therefore, are considered promising in the field of drug discovery and development [22]. ...
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DNA gyrase and topoisomerase IV are proven to be validated targets in the design of novel antibacterial drugs. In this study, we report the antibacterial evaluation and molecular docking studies of previously synthesized two series of cyclic diphenylphosphonates (1a–e and 2a–e) as DNA gyrase inhibitors. The synthesized compounds were screened for their activity (antibacterial and DNA gyrase inhibition) against ciprofloxacin-resistant E.coli and Klebsiella pneumoniae clinical isolates having mutations (deletion and substitution) in QRDR region of DNA gyrase. The target compound (2a) that exhibited the most potent activity against ciprofloxacin Gram-negative clinical isolates was selected to screen its inhibitory activity against DNA gyrase displayed IC50 of 12.03 µM. In addition, a docking study was performed with inhibitor (2a), to illustrate its binding mode in the active site of DNA gyrase and the results were compatible with the observed inhibitory potency. Furthermore, the docking study revealed that the binding of inhibitor (2a) to DNA gyrase is mediated and modulated by divalent Mg2+ at good binding energy (–9.08 Kcal/mol). Moreover, structure-activity relationships (SARs) demonstrated that the combination of hydrazinyl moiety in conjunction with the cyclic diphenylphosphonate based scaffold resulted in an optimized molecule that inhibited the bacterial DNA gyrase by its detectable effect in vitro on gyrase-catalyzed DNA supercoiling activity.
Article
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