Literature DB >> 18547805

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

Allan Urbach1, Giulio G Muccioli, Eric Stern, Didier M Lambert, Jacqueline Marchand-Brynaert.   

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.

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Year:  2008        PMID： 18547805     DOI： 10.1016/j.bmcl.2008.05.081

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  6 in total

Review 1.  The discovery and development of inhibitors of fatty acid amide hydrolase (FAAH).

Authors:  Katerina Otrubova; Cyrine Ezzili; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2011-06-28       Impact factor: 2.823

2.  Fluoride-mediated capture of a noncovalent bound state of a reversible covalent enzyme inhibitor: X-ray crystallographic analysis of an exceptionally potent α-ketoheterocycle inhibitor of fatty acid amide hydrolase.

Authors:  Mauro Mileni; Joie Garfunkle; Cyrine Ezzili; Benjamin F Cravatt; Raymond C Stevens; Dale L Boger
Journal:  J Am Chem Soc       Date:  2011-02-28       Impact factor: 15.419

3.  Reversible competitive α-ketoheterocycle inhibitors of fatty acid amide hydrolase containing additional conformational constraints in the acyl side chain: orally active, long-acting analgesics.

Authors:  Cyrine Ezzili; Mauro Mileni; Nicholas McGlinchey; Jonathan Z Long; Steven G Kinsey; Dustin G Hochstatter; Raymond C Stevens; Aron H Lichtman; Benjamin F Cravatt; Edward J Bilsky; Dale L Boger
Journal:  J Med Chem       Date:  2011-03-23       Impact factor: 7.446

4.  Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones.

Authors:  Yuesi Fang; Donald C Rogness; Richard C Larock; Feng Shi
Journal:  J Org Chem       Date:  2012-07-10       Impact factor: 4.354

5.  X-ray crystallographic analysis of alpha-ketoheterocycle inhibitors bound to a humanized variant of fatty acid amide hydrolase.

Authors:  Mauro Mileni; Joie Garfunkle; Cyrine Ezzili; F Scott Kimball; Benjamin F Cravatt; Raymond C Stevens; Dale L Boger
Journal:  J Med Chem       Date:  2010-01-14       Impact factor: 7.446

6.  Design, synthesis, and characterization of α-ketoheterocycles that additionally target the cytosolic port Cys269 of fatty acid amide hydrolase.

Authors:  Katerina Otrubova; Benjamin F Cravatt; Dale L Boger
Journal:  J Med Chem       Date:  2014-01-23       Impact factor: 7.446
  6 in total

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