Structure-activity relationships of kadsurenone analogues

J Med Chem. 1987 Jan;30(1):136-42. doi: 10.1021/jm00384a023.

Abstract

Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol. Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 X 10(-7) M, which is about 50% of the activity of the natural product (IC50 = 1 X 10(-7) M). The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Benzofurans / chemical synthesis*
  • Benzofurans / pharmacology
  • Blood Platelets / metabolism
  • Cell Membrane / metabolism
  • Circular Dichroism
  • Indicators and Reagents
  • Kinetics
  • Lignans*
  • Magnetic Resonance Spectroscopy
  • Platelet Activating Factor / antagonists & inhibitors*
  • Platelet Membrane Glycoproteins*
  • Rabbits
  • Receptors, Cell Surface / drug effects*
  • Receptors, Cell Surface / metabolism
  • Receptors, G-Protein-Coupled*
  • Structure-Activity Relationship

Substances

  • Benzofurans
  • Indicators and Reagents
  • Lignans
  • Platelet Activating Factor
  • Platelet Membrane Glycoproteins
  • Receptors, Cell Surface
  • Receptors, G-Protein-Coupled
  • platelet activating factor receptor
  • kadsurenone