alexa Lalita S Kumar, IJPRR 2014; 3(12) 20 Research Article Synthesis, Characterization and in vitro Anticancer Properties of 1-{5- Aryl-2-[5-(4-Fluoro-Phenyl)-Thiophen-2-yl]-[1,3,4]Oxadiazol-3-yl}-Ethanone

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Research Article

Lalita S Kumar, IJPRR 2014; 3(12) 20 Research Article Synthesis, Characterization and in vitro Anticancer Properties of 1-{5- Aryl-2-[5-(4-Fluoro-Phenyl)-Thiophen-2-yl]-[1,3,4]Oxadiazol-3-yl}-Ethanone

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A series of novel 1-{5-aryl-2-[5-(4-fluoro-phenyl)-thiophen-2-yl] [1, 3, 4] oxadiazol-3-yl}-ethanone derivatives 7a-f was synthesized by convergent synthetic method by using various carbohydrazides and 4-fluorophenyl thiophene-2-carboxaldehyde. The carboxaldehyde was reacted with various hydrazides in presence of catalytic amount of acetic acid and obtained Schiff base derivatives. The Schiff base derivatives were cyclized and acetylated in presence of acetic anhydride and obtained novel ethanone derivatives. The synthesized ethanone derivatives were purified by column-chromatography using silica gel (100-200 mesh). The synthesized compounds were evaluated for their anticancer properties using MTT assay. The 1, 3, 4-oxadiazole compounds have been synthesized from the corresponding Schiff base compounds 6a-f using acetic anhydride as promoter. The synthesized compounds were characterized on the basis of IR, 1H-NMR, 13C NMR and LCMS analyses. The in vitro cytotoxic evaluation of the synthesized heterocycles was carried out against HepG2, HeLa, MCF7 and Caco-2 cell lines. The standard used for the evaluation was 5-fluoro uracil. Most of the compounds in this series showed less cytotoxicity against all the cell lines used. One compound in this series(7d), i.e. 1-{5-[2-(4-fluorophenyl)pyridin-3-yl]-2-[5-(4-fluorophenyl)-thiophen-2-yl] [1, 3, 4] oxadiazol-3-yl}-ethanone was found to be active against breast cancer cell line (MCF7) which is comparable to the standard 5-fluorouracil and compounds 7b and 7e were moderately active against HepG2 cell line.


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