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Bioorg Med Chem. 2008 Sep 15;16(18):8745-59. doi: 10.1016/j.bmc.2008.07.041. Epub 2008 Jul 20.

Introduction of the 4-(4-bromophenyl)benzenesulfonyl group to hydrazide analogs of Ilomastat leads to potent gelatinase B (MMP-9) inhibitors with improved selectivity.

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Université de Reims-Champagne-Ardenne, CNRS UMR 6229, Institut de Chimie Moléculaire de Reims, Faculté de Pharmacie, IFR53 Biomolécules, 51 rue de Cognacq-Jay, 51096 Reims Cedex, France.


Hydrazide derivatives of Ilomastat, carrying either aryl groups or distinct alkyl and arylsulfonyl moieties were synthesized and evaluated for their MMP inhibitory activity. Potent and selective MMP-9 inhibition (IC(50)=3 nM) was observed for compound 3m (arylsulfonyl group: 4-(4-Br-C6H4)-C6H4-SO(2)-). Interaction with the S2 enzyme subsite is mainly responsible for the inhibitory properties of this derivative as confirmed by molecular docking computation.

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