Synthesis and evaluation of 2-amido-3-carboxamide thiophene CB₂ receptor agonists for pain management

Bioorg Med Chem Lett. 2012 Apr 1;22(7):2604-8. doi: 10.1016/j.bmcl.2012.01.121. Epub 2012 Feb 4.

Abstract

SAR studies on a series of thiophene amide derivatives provided CB(2) receptor agonists. The activity of the compounds was characterized by radioligand binding determination, multiple functional assays, ADME, and pharmacokinetic studies. A representative compound with selectivity for CB(2) over CB(1) effectively produced analgesia in behavioral models of neuropathic, inflammatory, and postsurgical pain. Control experiments using a CB(2) antagonist demonstrated the efficacy in the pain models resulted from CB(2) agonism.

MeSH terms

  • Amides / chemical synthesis*
  • Amides / pharmacokinetics
  • Amides / pharmacology
  • Analgesics / chemical synthesis*
  • Analgesics / pharmacokinetics
  • Analgesics / pharmacology
  • Animals
  • Biological Availability
  • Cell Line, Tumor
  • Dose-Response Relationship, Drug
  • Humans
  • Hyperalgesia / drug therapy*
  • Hyperalgesia / metabolism
  • Neuralgia / drug therapy*
  • Neuralgia / metabolism
  • Radioligand Assay
  • Rats
  • Rats, Sprague-Dawley
  • Receptor, Cannabinoid, CB1 / metabolism
  • Receptor, Cannabinoid, CB2 / agonists*
  • Receptor, Cannabinoid, CB2 / metabolism
  • Structure-Activity Relationship
  • Thiophenes / chemical synthesis*
  • Thiophenes / pharmacokinetics
  • Thiophenes / pharmacology

Substances

  • Amides
  • Analgesics
  • Receptor, Cannabinoid, CB1
  • Receptor, Cannabinoid, CB2
  • Thiophenes