Synthesis, antimicrobial evaluation, and docking studies of some novel benzofuran based analogues of chalcone and 1,4-benzodiazepine

A series of novel {5-[4-hydroxy-3-(4-phenyl-2,3-dihydro-1H-benzo[b][1,4]diazepin-2-yl)benzyl]- benzofuran-2-yl}(phenyl)methanones (5a–5g) were prepared by the condensation of (E)-3-{5-[(2- benzoylbenzofuran-5-yl)methyl]-2-hydroxyphenyl}-1-phenylprop-2-en-1-one (chalcone) (4a) with various substituted o-phenylene diamines in the presence of oxalic acid as catalyst. The structures of all compounds were characterized by FTIR, 1H NMR, 13C NMR, and MS. The representative examples were screened in vitro for antimicrobial activity. Among all compounds 4g and 5g showed potent antibacterial activity, 4b and 5g showed good antifungal activity. The data was further compared with structure based investigations using docking studies with the crystal structure of adenosine-5'-(β,γ-imido)triphosphate (2ONJ) from Staphylococcus aureus for antibacterial activity and trypsin (1FY5) protein from Fusarium oxysporum for the antifungal activity. The score values estimated by genetic algorithm were found to have a good correlation with the experimental inhibitory potencies.