Synthesis and pharmacology of 1-methoxy analogs of CP-47,497

Bioorg Med Chem. 2010 Aug 1;18(15):5475-82. doi: 10.1016/j.bmc.2010.06.054. Epub 2010 Jun 22.

Abstract

Three 1-methoxy analogs of CP-47,497 (7, 8, and 19) have been synthesized and their affinities for the cannabinoid CB(1) and CB(2) receptors have been determined. Although these compounds exhibit selectivity for the CB(2) receptor none have significant affinity for either receptor. Modeling and receptor docking studies were carried out, which provide a rationalization for the weak affinities of these compounds for either receptor.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Binding Sites
  • CHO Cells
  • Computer Simulation
  • Cricetinae
  • Cricetulus
  • Cyclohexanols / chemical synthesis
  • Cyclohexanols / chemistry*
  • Cyclohexanols / pharmacology
  • Humans
  • Receptor, Cannabinoid, CB1 / antagonists & inhibitors
  • Receptor, Cannabinoid, CB1 / metabolism
  • Receptor, Cannabinoid, CB2 / antagonists & inhibitors
  • Receptor, Cannabinoid, CB2 / metabolism
  • Structure-Activity Relationship

Substances

  • Cyclohexanols
  • Receptor, Cannabinoid, CB1
  • Receptor, Cannabinoid, CB2
  • CP 47497