Synthesis and Cytotoxic Evaluation of Pyran, Dihydropyridine and Thiophene Derivatives of 3-Acetylcoumarin

Chemical & Pharmaceutical Bulletin
Rafat M Mohareb, Nadia Y Megally Abdo

Abstract

A series of coumarin analogues bearing 4H-pyran rings 2a-d, 11a-d and 1,4-dihydropyridine rings 3a-d, 12a-d at position 3 were synthesized starting from either 3-acetyl coumarin (1) or the coumarin acetohydrazide derivative 4. Condensation of 3-acetylcoumarin (1) with 2-cyanoacetohydrazide afforded 2-cyano-N'-{1-[2-oxo-2H-chromen-3-yl]ethylidene}acetohydrazide (4). Reaction of compound 4 with elemental sulfur and either malononitrile or ethyl cyanoacetate afforded the thiophene derivatives 8 and 9, respectively. The structures of the newly synthesized compounds were confirmed on the basis of their spectral data and elemental analyses. All synthesized compounds were screened for their in vitro anticancer activity against six human cancer cell lines and normal fibroblasts. Several compounds showed potent inhibition with an IC50 value of ˂870 nM. Compound 3d exhibited equivalent cytotoxic effect as the standard CHS 828 against a breast cancer cell line (IC50 value=18 nM). Normal fibroblast cells (WI38) were affected to a much lesser extent (IC50 value >10000 nM).

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Citations

Apr 1, 2018·ChemMedChem·Pankaj Kumar Singh, Om Silakari
Oct 12, 2018·Topics in Current Chemistry·Hajar Hosseini, Mohammad Bayat
Feb 23, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Viviana Pardo-JiménezGuillermo Díaz-Araya
Dec 20, 2017·Anti-cancer Drugs·Flaviana Alves Dos SantosMaira Galdino da Rocha Pitta
Mar 7, 2021·Pharmaceutics·Consuelo RipollAngel Orte

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