Synthesis and biological activities of 2-hydroxyphenylacyl azoles and their oxime derivatives.

Abstract

Fourteen phenylacyl and 2-hydroxyphenylacyl azoles and their oxime derivatives of which three were new, 2-(2-methyl-1H-imidazol-1-yl)-1-phenylethanone oxime 7; 1-(2- hydroxyphenyl)-2-(2-methyl-1H-imidazol-1-yl)ethanone oxime 13 and 1-(2-hydroxyphenyl)- 2-(1H-1,2,4 traizol-1-yl)ethanone oxime 14. The yields obtained for the ketone derivatives were between 50 and 60%, and between 80 and 95% for the oxime derivatives. All compounds were characterized using NMR, IR, UV and GCMS, and were tested for their antifungal and antibacterial activity. These compounds possessed moderate antifungal and weak antibacterial activity, with compound 12, 1-(2-hydroxyphenyl)-2-(1H-imidazol-1- yl)ethanone oxime showing the highest antifungal activity with a MIC value of 1 μg mL̹̹̹⁻¹. In general, the 2'-hydroxy substituted compounds were shown to have better antifungal and antibacterial activity than the unsubstituted compounds.