Synthesis of methoxy-substituted chalcones and in vitro evaluation of their anticancer potential.

Chem Biol Drug Des

Pharmaceutical Chemistry Division, School of Advance Sciences, VIT University, Vellore, Tamil Nadu, 632 014, India; Organic and Medicinal Chemistry Research Laboratory, School of Advance Sciences, VIT University, Vellore, Tamil Nadu, 632 014, India.

Published: December 2013

AI Article Synopsis

  • Methoxy-substituted chalcones were synthesized using an efficient method involving 2-naphtylethanone and various aromatic aldehydes.
  • The compounds showed strong cytotoxic effects against three cancer cell lines, with detailed analyses indicating that their action led to apoptosis.
  • Among the tested compounds, 3c exhibited the highest cytotoxicity levels, while 3e demonstrated better IC50 values across all cell lines studied.

Article Abstract

Methoxy-substituted chalcones, 3 were obtained using simple, efficient method from 2-naphtylethanone, 1 and aromatic aldehydes, 2. The in vitro cytotoxicity activities of the chalcones against a panel of three human cancer cell lines were explored. The tested compounds were found to possess significant cytotoxic activity. The DNA strand break and damage was quantified through alkaline comet assay, flow cytometric analysis, and chromatin condensation studies, which revealed the apoptotic nature of the compounds. Compound 3c, (3-(3,4,5-trimethoxyphenyl)-1-(2-naphthyl) prop-2-en-1-one) showed highest cytotoxicity of 0.019 μm against HeLa, 0.020 μm against HCT15 and 0.022 μm against A549. Compound 3e, (3-(3,5-dimethoxyphenyl)-1-(2-naphthyl) prop-2-en-1-one) showed better IC50 values against all the three cell lines employed for the study.

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http://dx.doi.org/10.1111/cbdd.12184DOI Listing

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