Antiangiogenic activity of synthetic dihydrobenzofuran lignans

J Nat Prod. 2002 May;65(5):718-20. doi: 10.1021/np0103968.

Abstract

A series of synthetic dihydrobenzofuran lignans, obtained by biomimetic oxidative dimerization of caffeic or ferulic acid methyl ester followed by derivatization reactions, was tested for its antiangiogenic activity in the CAM (chorioallantoic membrane) assay. The dimerization product of caffeic acid methyl ester (2a) (methyl (E)-3-[2-(3,4-dihydroxyphenyl)-7-hydroxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate) showed a pronounced antiangiogenic activity, especially the 2R,3R-enantiomer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiogenesis Inhibitors / chemistry
  • Angiogenesis Inhibitors / isolation & purification*
  • Angiogenesis Inhibitors / pharmacology
  • Benzofurans / chemical synthesis*
  • Benzofurans / chemistry
  • Benzofurans / pharmacology
  • Caffeic Acids / chemistry
  • Catalysis
  • Chorion / drug effects
  • Chromatography, High Pressure Liquid
  • Lignans / chemical synthesis*
  • Lignans / chemistry
  • Lignans / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Propionates / chemical synthesis*
  • Propionates / chemistry
  • Propionates / pharmacology
  • Stereoisomerism

Substances

  • Angiogenesis Inhibitors
  • Benzofurans
  • Caffeic Acids
  • Lignans
  • Propionates
  • methyl-3-(2-(3,4-dihydroxyphenyl)-7-hydroxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl)prop-2-enoate