Design, synthesis and biological activity of novel oxadiazole containing monoacylglycerols as potential bioactive lipids

Abstract

A series of novel 1,3,4-oxadiazole based 1-monoacylglycerol derivatives were synthesized and evaluated for their antimicrobial and anticancer activity. Eight different substituted benzoic acids were utilized for the synthesis of new fatty acids incorporating the 1,3,4-oxadiazole scaffold. These fatty acids were further employed for the preparation of 1-monoacylglycerols (10a-10 h) in an eight step synthetic route. The synthesized 1-monoacylglycerols were characterized by NMR, IR and MS spectral data and screened for their in vitro antimicrobial activity against selected bacterial and fungal strains. The best results were obtained for 3,4-dimethoxybenzoic acid (10c), benzoic acid (10a) and 4-methoxybenzoic acid (10b) derivatives with a noticeable zone of inhibition on all the tested organisms. In the in vitro cytotoxicity assay against B16-F10, DU145, Hep G2 and CHO-K1 cell lines, the 2,3,4-trimethoxybenzoic acid (10d) and 4-fluorobenzoic acid derivative (10e) showed a broad spectrum of cytotoxicity. Based on the preliminary screening it can be suggested that these novel lipidic oxadiazole derivatives could act as promising antitumor agents with some degree of therapeutic effect and further studies can help in designing potential analogs.