1. J Med Chem. 2009 Nov 26;52(22):7054-7068. beta-Lactams Derived from a Carbapenem Chiron Are Selective Inhibitors of Human Fatty Acid Amide Hydrolase versus Human Monoacylglycerol Lipase. Feledziak M, Michaux C, Urbach A, Labar G, Muccioli GG, Lambert DM, Marchand-Brynaert J. Unite de Chimie Organique et Medicinale, Universite Catholique de Louvain, Batiment Lavoisier, Place Louis Pasteur 1, B-1348 Louvain-La-Neuve, Belgium. A library of 30 beta-lactams has been prepared from (3R,4R)-3-[(R)-1'-(tbutyldimethylsilyloxy)-ethyl]-4-acetoxy-2-azetidinone, and the corresponding deacetoxy derivative, by sequential N- and O-functionalizations with various omega-alkenoyl and omega-arylalkanoyl chains. All compounds were selective inhibitors of hFAAH versus hMGL, and IC(50) values in the nanomolar range (5-14 nM) were recorded for the best representatives. From time-dependent preincubation and rapid dilution studies, and from docking analyses in a homology model of the target enzyme, a reversible mechanism of inhibition of hFAAH is proposed. PMID: 19877691 [PubMed - as supplied by publisher]