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ID: ALA4480386
Journal: Eur J Med Chem
Title: Synthesis and anticancer evaluation of new lipophilic 1,2,4 and 1,3,4-oxadiazoles.
Authors: Caneschi W, Enes KB, Carvalho de Mendonça C, de Souza Fernandes F, Miguel FB, da Silva Martins J, Le Hyaric M, Pinho RR, Duarte LM, Leal de Oliveira MA, Dos Santos HF, Paz Lopes MT, Dittz D, Silva H, Costa Couri MR.
Abstract: A series of1,2,4- and 1,3,4-oxadiazole derivatives were synthesized and evaluated for their anticancer activity. Halogenated 1,2,4-oxadiazoles were obtained from benzonitrile and coupled either lipophilic amines or with aminoalcohols. Lipophilic 1,3,4-oxadiazole derivatives were obtained through the Mannich reactions between 5-(aryl)-1,3,4-oxadiazole-2-thiol and alkylated or acylated amines. The in vitro cytotoxic effects were evaluated against 4T1- mammary carcinoma and CT26 - colon cancer cells. The best results were obtained for the 1,3,4-oxadiazole coupled to alkylated piperazine with 10-14 carbon chain moiety, with IC50 values ranging from 1.6 to 3.55μΜ for the 4T1 cell line, and from 1.6 to 3.9 μM for the CT26.WT cell line, and selectivity index up to 19. The most potent compounds were investigated with AnnexinV and PI staining as indicative of apoptosis induction.
CiteXplore: 30654237