Synthesis and inhibition of PGE2 production of 6,8-disubstituted chrysin derivatives

Eur J Med Chem. 2005 Sep;40(9):943-8. doi: 10.1016/j.ejmech.2005.04.013. Epub 2005 Jun 15.

Abstract

A series of 6,8-disubstituted chrysin derivatives have been synthesized and evaluated for their PGE2 inhibitory activities. 6,8-Disubstituted chrysin derivatives were obtained from naturally occurring chrysin by halogenation, oxidation, thiomethylation and C-C cross coupling reaction. Among the compounds investigated, 6,8-dibromochrysin (2), 6,8-diiodochrysin (4), 6,8-dimethylthiochrysin (9) and 6,8-dimethoxychrysin (11) showed as strong inhibitory activities of PGE2 production from LPS-induced RAW 264.7 cells as wogonin, a well known natural flavone having strong and selective COX-2 inhibitory activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Cyclooxygenase 2 Inhibitors / chemical synthesis
  • Cyclooxygenase 2 Inhibitors / pharmacology
  • Dinoprostone / antagonists & inhibitors
  • Dinoprostone / metabolism*
  • Drug Evaluation, Preclinical
  • Flavonoids / chemical synthesis*
  • Flavonoids / chemistry
  • Flavonoids / pharmacology*
  • Macrophages / drug effects
  • Mice
  • Molecular Structure

Substances

  • Cyclooxygenase 2 Inhibitors
  • Flavonoids
  • chrysin
  • Dinoprostone