3-Alkenyl-2-azetidinones as fatty acid amide hydrolase inhibitors

Bioorg Med Chem Lett. 2008 Jul 15;18(14):4163-7. doi: 10.1016/j.bmcl.2008.05.081. Epub 2008 May 24.

Abstract

A series of novel 2-azetidinones (beta-lactams) bearing short alkenyl chains at C3 and N1 have been prepared and evaluated in vitro as inhibitors of human FAAH. Compound 9c (1-(4'-pentenoyl-3-(4'-pentenyl)-2-azetidinone)) featured an IC(50) value of 4.5 microM and a good selectivity for FAAH versus MGL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidohydrolases / antagonists & inhibitors*
  • Animals
  • Azetidines / pharmacology*
  • Chemistry, Pharmaceutical / methods*
  • Drug Design
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Escherichia coli / metabolism
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Pancreatic Elastase / antagonists & inhibitors
  • Swine
  • beta-Lactams / chemistry

Substances

  • 2-azetidinone
  • Azetidines
  • Enzyme Inhibitors
  • beta-Lactams
  • Pancreatic Elastase
  • Amidohydrolases
  • fatty-acid amide hydrolase