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

• Published in: Farmaco (Società chimica italiana : 1989) 2001-12, Vol.56 (12), p.975-979
• Main Authors: Kocabalkanli, Ayşe, Ateş, Öznur, Ötük, Gülten
• Format: Article
• Language: English
• Subjects: 5-Aryl-2-[[α-(4-substituted benzoyloxy)-α-phenylacetyl or methylacetyl]amino]-1,3,4-oxadiazoles; Anti-Bacterial Agents; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - pharmacology; Antibacterial agents; Antibacterial drugs; Antibiotics. Antiinfectious agents. Antiparasitic agents; Bacteria - drug effects; Biological and medical sciences; Fungi - drug effects; Medical sciences; Microbial Sensitivity Tests; Microbiology; Oxadiazoles - chemical synthesis; Oxadiazoles - pharmacology; Pharmacology. Drug treatments; Structure-Activity Relationship; Synthesis
• ISSN: 0014-827X; 1879-0569
• DOI: 10.1016/S0014-827X(01)01158-2

In this study, a new series of 2-[[α-(4-substitutedbenzoyloxy)-α-phenylacetyl or methylacetyl]amino]-5-(4-methoxyphenyl)-1,3,4-oxadiazoles were obtained by condensation of 2-[(α-chloro-α-phenylacetyl or α-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, 1H 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 μg ml −1, respectively) and compound 4e against S. epidermidis ATCC 12228 (MIC, 156 μg ml −1).