Synthesis and SAR of 5,6-diarylpyridines as human CB1 inverse agonists

Bioorg Med Chem Lett. 2005 Feb 1;15(3):645-51. doi: 10.1016/j.bmcl.2004.11.031.

Abstract

Structure-activity relationship studies for two series of 2-benzyloxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyridines having either a 3-cyano or 3-carboxamide moiety resulted in the preparation of the 2-(3,4-difluorobenzyloxy)-3-nitrile analog 10d and the 2-(3,4-difluorobenzyloxy)-3-(N-propylcarboxamide) analog 16c, (hCB1 IC(50)=1.3 and 1.7 nM, respectively) as potent and selective hCB1 inverse agonists. Their synthesis and biological activities are described herein.

MeSH terms

  • Animals
  • Biological Availability
  • CHO Cells
  • Cricetinae
  • Humans
  • Inhibitory Concentration 50
  • Male
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacokinetics
  • Pyridines / pharmacology
  • Radioligand Assay
  • Rats
  • Rats, Sprague-Dawley
  • Receptor, Cannabinoid, CB1 / agonists*
  • Structure-Activity Relationship
  • Tissue Distribution
  • Transfection

Substances

  • Pyridines
  • Receptor, Cannabinoid, CB1