Design, synthesis and cytotoxic evaluation of o-carboxamido stilbene analogues

Int J Mol Sci. 2013 Nov 27;14(12):23369-89. doi: 10.3390/ijms141223369.

Abstract

Resveratrol, a natural stilbene found in grapes and wines exhibits a wide range of pharmacological properties. Resveratrol is also known as a good chemopreventive agent for inhibiting carcinogenesis processes that target kinases, cyclooxygenases, ribonucleotide reductase and DNA polymerases. A total of 19 analogues with an amide moiety were synthesized and the cytotoxic effects of the analogues on a series of human cancer cell lines are reported. Three compounds 6d, 6i and 6n showed potent cytotoxicity against prostate cancer DU-145 (IC50=16.68 µM), colon cancer HT-29 (IC50=7.51 µM) and breast cancer MCF-7 (IC50=21.24 µM), respectively, which are comparable with vinblastine. The resveratrol analogues were synthesized using the Heck method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anticarcinogenic Agents / chemical synthesis*
  • Anticarcinogenic Agents / chemistry
  • Anticarcinogenic Agents / toxicity
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Drug Design*
  • Drug Screening Assays, Antitumor
  • HT29 Cells
  • Humans
  • MCF-7 Cells
  • Resveratrol
  • Stilbenes / chemical synthesis
  • Stilbenes / chemistry*
  • Stilbenes / toxicity

Substances

  • Anticarcinogenic Agents
  • Stilbenes
  • Resveratrol