Structure-cytotoxic activity relationship of 3-arylideneflavanone and chromanone (E,Z isomers) and 3-arylflavones

Bioorg Med Chem Lett. 2013 Jul 15;23(14):4102-6. doi: 10.1016/j.bmcl.2013.05.044. Epub 2013 May 23.

Abstract

The E,Z-isomers of 3-arylidene substituted flavanone, chromanone and 3-aryl substituted flavone derivatives were tested in vitro for their cytotoxic activity against three cancer cell lines (HL-60, NALM-6, WM-115) and normal cell line (HUVEC). It was observed that substitution at C3 position led to significant enhance in cytotoxicity. Isomeric configuration of 3-arylideneflavanones had an influence on the cytotoxic potential. Multiple regression analysis combined with variable selection by genetic algorithm was used to model relationships between molecular descriptors and the cytotoxic activity. The most accurate QSAR models were based on a combination between energy of LUMO, experimental value of logP and partial charge on carbonyl oxygen (δO2).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Chromans / chemistry*
  • Chromans / toxicity
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Flavanones / chemistry*
  • Flavanones / toxicity
  • HL-60 Cells
  • Human Umbilical Vein Endothelial Cells
  • Humans
  • Molecular Conformation
  • Quantitative Structure-Activity Relationship
  • Stereoisomerism

Substances

  • Chromans
  • Flavanones
  • flavanone