Synthesis and biological screening of a combinatorial library of β-chlorovinyl chalcones as anticancer, anti-inflammatory and antimicrobial agents

A combinatorial library of beta-chlorovinyl chalcones ( 4) were synthesized by Claisen-Schmidt condensation reaction. Catalytic reaction of substituted 3-chloro-3-phenyl-propenal ( 2) and 1-(2,4-dimethoxyphenyl)-ethanone or 1-(4-methoxy-phenyl)-ethanone ( 3) in alkaline conditions furnished the target compound 5-chloro-1-(2,4-dimethoxy-phenyl)-5-phenyl-penta-2,4-dien-1-one ( 4). The synthesized compounds were screened for their biological activity viz. anticancer, anti-inflammatory and antimicrobial activities. Synthesized compounds 4g and 4h revealed promising anti-inflammatory activity (66-67% TNF-alpha and 95-97% IL-6 inhibitory activity at 10 mu M). Cytotoxicity of the compounds checked using CCK-8 cell lines and found to be nontoxic to slightly toxic. Furthermore, the anticancer activity (30-40%) was shown by compounds 4d, 4e, 4h and 4b at 10 mu M concentrations against ACHN followed by Calu 1, Panc1, HCT116 and H460 cell lines. Some of the compounds 4d, 4e, 4a, 4i and 4b revealed promising antimicrobial activity at MIC 50-100 mu g/mL against selected pathogenic bacteria and fungi. (C) 2010 Published by Elsevier Ltd.