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■ Synthesis, Characterization and Biological Activity of Some Novel Coumarin Derivatives Containing Pyridine Moiety

Ahmed A. Fadda,* Khaled S. Mohamed, Hala M. Refat, and Engy E. El-Bialy

*Department of Chemistry, Faculty of Science, University of Mansoura, Mansoura 35516, Egypt

Abstract

The 2-acetyl-3H-benzo[f]chromen-3-one (1) was used as a key intermediate for the synthesis of 3-(1-amino-3-oxo-3H-benzo[f]chromen-2-yl) - but-2-enenitrile derivatives 3a-d via condensation reactions with activated nitrile derivatives in the presence of ammonium acetate. Moreover, the 3a-d underwent interamolecular cyclization to form 3-alkyl-2-amino-4-methyl-5-oxo-5H-benzo [5, 6]chromeno[4,3-b]pyridine 4a-d. Compound 1 reacts with acetophenone and cyclohexanone in the presence of cyanoacetamide to afford the benzo[5,6]chromeno[3,4-c]pyridin-5-one derivatives 5 and 6, respectively. Also, 4-aryl-6-[benzo[h]coumarin-3-yl]-3-cyano-2-pyridone derivatives 8a-d were synthesized by an efficient and convenient method by the one-pot reaction of 1 with aromatic aldehydes 7a-d and malononitrile in the presence of sodium hydroxide under a solvent free condition. This method has the advantages of mild reaction conditions, easy workup and inexpensive reagents. Moreover, 2-(4,6-diphenylpyridin-2-yl)-3H-benzo[f]chromen-3-one (16) was prepared via reaction of α-pyrdinium salt of methyl ketone of 1 with benzalacetophenone in the presence of ammonium acetate. The structures of the new synthesized compounds were confirmed by spectral data and elemental analyses. Newly compounds were tested for in vitro cytotoxicity against heptacelluar carcinoma (HepG2) and breast cancer (MCF-7) in addition to their antibacterial evaluation.