Abstract
A series of 1,3,4-oxadiazole-2-thiol incorporating fatty acid moieties was synthesized. The chemical structure of the synthesized compounds was established by their spectral data, elemental analysis, and their chemical behavior. Their thioglycosides derivatives and the analogous 1,2,4-triazole were also prepared. The in vitro cytotoxicty of the synthesized compounds was screened against two cell lines; breast cell line MCF-7, and liver cell line HepG2. The most potent compound is (E)-5-(heptadec-8-enyl)-1,3,4-oxadiazole-2-thiol 4f with IC50 (2.82 | µg/ml) and (3.87 µg/ml) against breast cell line MCF-7 and liver cell line HepG2 respectively. Molecular Docking study of Bcl-2 was conducted for the most potent compound, its analogues and the lowest cytotoxicty compound. The antimicrobial activity was also screened, compound (E)-5-ethyl-1,3,4-oxadiazole-2-thiol 4a showed a broad spectrum of activity. A relationship between the length of the fatty acid chain and the biological activity was noticed in the tested compounds.
Keywords: Antifungal, Antimicrobial, Antitumor, Fatty acids, 1, 3, 4-oxadiazole-2-thiol.
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