Synthesis, characterization and biological activity of 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl)propanoic acid derivatives

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Abstract

A series of six novel 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl)propanoic acids and six corresponding methyl esters were synthesized. All compounds were characterized by melting points, elemental analysis, FT-IR, 1H and 13C NMR spectroscopy. Crystal structure of methyl-2-(5-(4-methoxybenzylidene)-2,4–dioxotetrahydrothiazole-3-yl)propionate was confirmed by X-ray analysis. The antiproliferative activity of all synthesized compounds against human colon cancer, breast cancer and myelogenous leukemia cell lines, i.e. HCT-116, MDA-231 and K562, respectively, was evaluated. The results indicate that antiproliferative activity of the synthesized esters is better than the activity of the corresponding acids. All synthesized compounds showed significant antiproliferative effects against HCT116 cells in all tested concentrations (0.01–100 μM). Moreover, in vitro antimicrobial activity against a wide range of tested microorganisms was examined.

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Božić, B., Rogan, J., Poleti, D., Rančić, M., Trišović, N., Božić, B., & Ušćumlić, G. (2017). Synthesis, characterization and biological activity of 2-(5-arylidene-2,4-dioxotetrahydrothiazole-3-yl)propanoic acid derivatives. Arabian Journal of Chemistry, 10, S2637–S2643. https://doi.org/10.1016/j.arabjc.2013.10.002

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