Novel 3-phenylprop-2-ynylamines as inhibitors of mammalian squalene epoxidase

Org Biomol Chem. 2003 Feb 7;1(3):498-506. doi: 10.1039/b209165h.

Abstract

The synthesis of a novel series of 3-phenylprop-2-ynylamines as selective mammalian squalene epoxidase inhibitors is described. Structure activity relationship studies led to the discovery of compound 19, 1-[3-(3,5-dichlorophenyl)-prop-2-ynyl]-3- methylpiperidine hydrochloride with an IC50 of 2.8 +/- 0.6 microM against rat liver squalene epoxidase. Against 23 strains of fungal squalene epoxidase compound 19 was found to be inactive.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemical synthesis
  • Amines / chemistry*
  • Amines / pharmacology*
  • Animals
  • Benzene Derivatives / chemistry
  • Benzene Derivatives / pharmacology
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Female
  • Inhibitory Concentration 50
  • Oxygenases / antagonists & inhibitors*
  • Rats
  • Rats, Sprague-Dawley
  • Squalene Monooxygenase
  • Structure-Activity Relationship

Substances

  • Amines
  • Benzene Derivatives
  • Enzyme Inhibitors
  • Oxygenases
  • Squalene Monooxygenase