Synthesis and pharmacological evaluation of sulfamide-based analogues of anandamide

Eur J Med Chem. 2009 Dec;44(12):4889-95. doi: 10.1016/j.ejmech.2009.08.003. Epub 2009 Aug 12.

Abstract

Arachidonyl and linoleyl sulfamide derivatives have been synthesized and their potential cannabimimetic properties evaluated in in vitro functional and binding assays. Replacement of the ethanolamide moiety of anandamide by -CH(2)NHSO(2)NH-R considerably reduces the CB1 receptor activity and only some of the compounds showed modest cannabinoid properties in binding assays. The new compounds were also tested as inhibitors of the FAAH enzyme but were inactive.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidohydrolases / antagonists & inhibitors
  • Animals
  • Arachidonic Acids / chemical synthesis*
  • Arachidonic Acids / chemistry
  • Arachidonic Acids / pharmacology*
  • Cannabinoid Receptor Modulators / chemical synthesis*
  • Cannabinoid Receptor Modulators / chemistry
  • Cannabinoid Receptor Modulators / pharmacology*
  • Cells, Cultured
  • Endocannabinoids
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Male
  • Molecular Structure
  • Polyunsaturated Alkamides / chemical synthesis*
  • Polyunsaturated Alkamides / chemistry
  • Polyunsaturated Alkamides / pharmacology*
  • Rats
  • Sulfonamides*
  • Vas Deferens / drug effects

Substances

  • Arachidonic Acids
  • Cannabinoid Receptor Modulators
  • Endocannabinoids
  • Enzyme Inhibitors
  • Polyunsaturated Alkamides
  • Sulfonamides
  • Amidohydrolases
  • fatty-acid amide hydrolase
  • anandamide