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J Med Chem. 2009 Nov 26;52(22):7054-68. doi: 10.1021/jm9008532.

beta-Lactams derived from a carbapenem chiron are selective inhibitors of human fatty acid amide hydrolase versus human monoacylglycerol lipase.

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1
Unite de Chimie Organique et Medicinale, Universite Catholique de Louvain, Batiment Lavoisier, Place Louis Pasteur 1, B-1348 Louvain-La-Neuve, Belgium.

Abstract

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
DOI:
10.1021/jm9008532
[Indexed for MEDLINE]
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