Synthesis and evaluation of antibacterial activity of some 2-[[alpha-(4-substituted benzoyloxy)-alpha-phenylacetyl or methylacetyl]amino]-5-(4-methoxyphenyl)-1,3,4-oxadiazoles

Abstract

In this study, a new series of 2-[[alpha-(4-substitutedbenzoyloxy)-alpha-phenylacetyl or methylacetyl]amino]-5-(4-methoxyphenyl)-1,3,4-oxadiazoles were obtained by condensation of 2-[(alpha-chloro-alpha-phenylacetyl or alpha-bromopropionyl)amino]-5-(4-methoxyphenyl)1,3,4-oxadiazoles with sodium salts of 4-substituted benzoic acids. Structures of the compounds were assigned on the basis of spectral data (UV, IR, H-1 NMR, EI MS) and elemental analyses. The antibacterial activities of the novel compounds against Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, Escherichia coli ATCC 8739, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa ATCC 1539, Salmonella typhi, Shigella flexneri and Proteus mirabilis and antifungal activity against Candida albicans ATCC 10231 were tested using disk diffusion method. Compounds 4a, 4d and 4g were found to be active against S. aureus ATCC 6538 (MIC, 78, 39 and 78 mug ml(-1), respectively) and compound 4e against S. epidermidis ATCC 12228 (MIC, 156 mug ml(-1)). (C) 2001 Elsevier Science S.A. All rights reserved.