Convergent synthesis and preliminary biological evaluations of the stilbenolignan (+/-)-aiphanol and various congeners

Org Biomol Chem. 2003 Jul 21;1(14):2427-9. doi: 10.1039/b305106d.

Abstract

Treatment of an equimolar mixture of stilbene 7 and cinnamyl alcohol 8 with silver carbonate in acetone-benzene afforded a ca. 2:1:2:1 mixture of the stilbenolignan (+/-)-aiphanol (1) and congeners 2-4 each of which show significant anti-angiogenic and COX-2 inhibitory properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiogenesis Inhibitors / chemical synthesis
  • Angiogenesis Inhibitors / pharmacology
  • Animals
  • Aorta / drug effects
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors / chemical synthesis
  • Cyclooxygenase Inhibitors / pharmacology
  • Dose-Response Relationship, Drug
  • Inhibitory Concentration 50
  • Isoenzymes / antagonists & inhibitors
  • Magnetic Resonance Spectroscopy
  • Membrane Proteins
  • Prostaglandin-Endoperoxide Synthases
  • Rats
  • Stereoisomerism
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry*
  • Stilbenes / pharmacology*

Substances

  • Angiogenesis Inhibitors
  • Cyclooxygenase 2 Inhibitors
  • Cyclooxygenase Inhibitors
  • Isoenzymes
  • Membrane Proteins
  • Stilbenes
  • aiphanol
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Prostaglandin-Endoperoxide Synthases
  • Ptgs1 protein, rat