Design, synthesis, and biological evaluation of novel alkenylthiophenes as potent and selective CB1 cannabinoid receptor antagonists

Org Biomol Chem. 2008 Feb 7;6(3):447-50. doi: 10.1039/b716434c. Epub 2007 Dec 10.

Abstract

A novel class of (5-(pent-1-enyl)thiophen-2-yl)pyrazole antagonists was discovered, many of which exhibited potent CB1 activity and good CB1/2 selectivity, suggesting that along with a 1,3-transposition of the carbonyl of the pyrazole 3-carboxamide, bioisosteric replacement of the conventional pyrazole 5-aryl group with a thienyl ring substituted with an appropriate alkenyl moiety is viable.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drug Design*
  • Humans
  • Inhibitory Concentration 50
  • Receptor, Cannabinoid, CB1 / antagonists & inhibitors*
  • Receptor, Cannabinoid, CB1 / metabolism
  • Receptor, Cannabinoid, CB2 / antagonists & inhibitors
  • Receptor, Cannabinoid, CB2 / metabolism
  • Substrate Specificity
  • Thiophenes / chemical synthesis*
  • Thiophenes / chemistry
  • Thiophenes / metabolism
  • Thiophenes / pharmacology*

Substances

  • Receptor, Cannabinoid, CB1
  • Receptor, Cannabinoid, CB2
  • Thiophenes