Synthesis of fatty acid amides of catechol metabolites that exhibit antiobesity properties

ChemMedChem. 2010 Oct 4;5(10):1781-7. doi: 10.1002/cmdc.201000161.

Abstract

A series of fatty acid amides of 3,4-methylenedioxymethamphetamine (MDMA) catechol metabolites were synthesized in order to evaluate their biological activities. Upon administration, all synthesized compounds resulted in negative modulation of food intake in rats. The most active compounds have affinity for the CB(1) receptor and/or PPAR-α; part of their biological activity may be caused by these double interactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Amides / pharmacology
  • Animals
  • Anti-Obesity Agents / chemical synthesis*
  • Anti-Obesity Agents / chemistry
  • Anti-Obesity Agents / pharmacology
  • Catechols / chemistry
  • Catechols / metabolism*
  • Fatty Acids / chemistry*
  • Kinetics
  • Male
  • N-Methyl-3,4-methylenedioxyamphetamine / chemistry
  • N-Methyl-3,4-methylenedioxyamphetamine / metabolism
  • PPAR alpha / chemistry
  • PPAR alpha / metabolism
  • Rats
  • Rats, Wistar
  • Receptor, Cannabinoid, CB1 / chemistry
  • Receptor, Cannabinoid, CB1 / metabolism

Substances

  • Amides
  • Anti-Obesity Agents
  • Catechols
  • Fatty Acids
  • PPAR alpha
  • Receptor, Cannabinoid, CB1
  • N-Methyl-3,4-methylenedioxyamphetamine
  • catechol