Synthesis, antimicrobial evaluation and docking studies of oxazolone-1,2,3-triazole-amide hybrids

In an attempt to develop quality antimicrobial agents, a series of oxazolone-1,2,3-triazole-amide hybrids were obtained from oxazolone tethered with a terminal alkyne and in situ generated 2-azido-N-phenylacetamides. All the synthesized compounds were characterized by using various spectroscopic techniques. The developed hybrids were evaluated for their in vitro antimicrobial activity toward three Gram-positive bacteria S. aureus, B. subtilis and S. gorodonii and three Gram-negative bacteria-E. coli, S. enterica and P. aeruginosa-and two fungi, viz. C. albicans and A. niger. Oxazolone-amide-1,2,3-triazoles (8a-e, 9a-e, 10a-e) exhibited almost 15 times better efficacy than alkyne precursors, i.e., oxazolone-linked terminal alkynes (6a-c). Compound 10d exhibited very good antimicrobial activity toward all the tested microorganisms. Docking studies of compounds 10d and 6c were also carried out in the binding site of enzyme sterol-14-alpha-demethylase of C. albicans, which supported the in vitro experimental results.