MICROWAVE ASSISTED SYNTHESIS, CHARACTERIZATION, MOLECULAR DOCKING AND ANTIMICROBIAL EVALUATION OF 4-NITROCINNAMIDE ANALOGUES

A series of novel 2-Benzamido-3-(4-nitrophenyl)-N’-(substituted) benzylidene-acrylohydrazide (4a-l) analogues were designed by incorporating the few pharmacophoric fragments to enhance the activity profile of molecules. Title compounds were synthesized by the microwave irradiation of α-Benzamido-(4-nitro)-cinnamahydrazide (3) reveals with aromatic/ heteroaromatic aldehydes under acidic conditions, characterized by IR, ¹H & ¹³C NMR, Mass and evaluated for antimicrobial activity by using Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis and Candida albicans strains. Compounds 4e and 4k exhibited significant protection against bacterial strains (MIC: 3.12-50µg/ml; 3.12-100µg/ml respectively) and compound 4h showed better activity (MIC: 12.5 µg/ml) against fungal strain. And also molecular docking interactions with FAB protein for evaluating the antimicrobial activity was done by using XP GLIDE module of Schrodinger suite and this study highlights, all the analogues exhibited significant affinity towards the 5BNM (FAB Protein) have good docking scores (-4.51 to -8.78) than standard drug ciprofloxacin (-4.74). Of the 12 new analogues, compound 4e was identified as most active ligand with good activity profile against bacterial strains and also have higher binding affinity with target.