Structure-activity relationships of 2-arylamido-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxamide derivatives as cannabinoid receptor agonists and their analgesic action

Bioorg Med Chem Lett. 2012 Dec 15;22(24):7314-21. doi: 10.1016/j.bmcl.2012.10.087. Epub 2012 Oct 25.

Abstract

SAR studies were performed on a series of 2-arylamido-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxamide derivatives as cannabinoid receptor agonists. Starting from a HTS hit both potency and selectivity could be improved. Modifications to the thiophene fusion and C-3 amides were studied. A representative compound 3t produced analgesia when dosed orally in inflammatory pain models of writhing and carrageenan-induced allodynia.

MeSH terms

  • Animals
  • Humans
  • Molecular Structure
  • Pyrans / chemical synthesis
  • Pyrans / chemistry
  • Pyrans / pharmacology*
  • Rats
  • Receptors, Cannabinoid / metabolism*
  • Structure-Activity Relationship
  • Thiophenes / chemical synthesis
  • Thiophenes / chemistry
  • Thiophenes / pharmacology*

Substances

  • Pyrans
  • Receptors, Cannabinoid
  • Thiophenes