Design and synthesis of (13S)-methyl-substituted arachidonic acid analogues: templates for novel endocannabinoids

Chemistry. 2010 Apr 6;16(13):4091-9. doi: 10.1002/chem.200902880.

Abstract

Two novel methyl-substituted arachidonic acid derivatives were prepared in an enantioselective manner from commercially available chiral building blocks, and were found to be excellent templates for the development of (13S)-methyl-substituted anandamide analogues. One of the compounds synthesized, namely, (13S,5Z,8Z,11Z,14Z)-13-methyl-eicosa-5,8,11,14-tetraenoic acid N-(2-hydroxyethyl)amide, is an endocannabinoid analogue with remarkably high affinity for the CB1 cannabinoid receptor.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Arachidonic Acid / chemical synthesis*
  • Arachidonic Acid / chemistry
  • Arachidonic Acids / chemical synthesis*
  • Arachidonic Acids / chemistry
  • Cannabinoid Receptor Modulators / chemistry*
  • Cannabinoid Receptor Modulators / metabolism
  • Endocannabinoids*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Receptor, Cannabinoid, CB1 / chemistry*
  • Receptor, Cannabinoid, CB1 / metabolism
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • (13S,5Z,8Z,11Z,14Z)-13-methyl-eicosa-5,8,11,14-tetraenoic acid N-(2-hydroxyethyl)amide
  • Arachidonic Acids
  • Cannabinoid Receptor Modulators
  • Endocannabinoids
  • Receptor, Cannabinoid, CB1
  • Arachidonic Acid