Antimicrobial activity of novel substituted 1,2,4-triazole and 1,3-thiazole derivatives

Abstract

In this work, thirteen new compounds have been synthesized, characterized and evaluated for their antifungal and antimicrobial activities. Seven of them which contain the thiazole ring were obtained by reacting 2-(2-(2-methoxyphenoxy)propanoyl)-N-phenylhydrazine-1-carbothioamide (3) with phenylacyl bromide derivatives, while the other six compounds that have the 1,2,4-triazole ring (6a-6f) were prepared through couple of steps starting from the same intermediate 2-(2-(2-methoxyphenoxy)acetyl)-N-phenylhydrazine-1-carbothioamide (3). All final compounds were characterized using LC-MS, (HNMR)-H-1 and (CNMR)-C-13 spectroscopic techniques. All compounds were tested against twelve bacterial strains and ten fungus species. Derivative (5a) that is N'-(3,4-diphenylthiazol-2(3H)-ylidene)-2(methoxyphenoxy)propanehydrazide had shown the best activity and selectivity toward Yersinia enterocolitica bacterial type. All compounds demonstrated good activity against filamentous fungi species compared to yeast species. Molecular docking studies also showed that derivatives 2-(2-Methoxyphenoxy)-N'-(4-(4-methoxyphenyl)-3-phenylthiazol-2(3H)-ylidene)propanehydrazide (5c), N'-(4-(4-chlorophenyl)-3-phenylthiazol-2(3H)-ylidene)-2-(2-methoxyphenoxy)propanehydrazide (5d) and N-(4-(4-fluorophenyl)-3-phenylthiazol-2(3H)-ylidene)-2-(2-methoxyphenoxy)propanehydrazide (5e) interacted with the active cavity of lanosterol 14 alpha-demethylase enzyme.