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Bioorg Med Chem Lett. 2008 Jun 1;18(11):3333-7. doi: 10.1016/j.bmcl.2008.04.035. Epub 2008 Apr 16.

Novel bis-(arylsulfonamide) hydroxamate-based selective MMP inhibitors.

Author information

1
Department of Pharmaceutical Sciences, North Dakota State University, 1401 Albrecht Blvd, Fargo, ND 58105, USA.

Abstract

A series of bis-(arylsulfonamide) hydroxamate inhibitors were synthesized. These compounds exhibit good potency against MMP-7 and MMP-9 depending on the nature, steric bulk, and substitution pattern of the substituents in the benzene ring. In general, the preliminary structure-activity relationships (SAR) suggest that among the DAPA hydroxamates (i) electron-rich benzene rings of the sulfonamides may produce better inhibitors than electron-poor analogs. However, potential H-bond acceptors can reverse the trend depending on the isozyme; (ii) isozyme selectivity between MMP-7 and -9 can be conferred through steric bulk and substitution pattern of the substituents in the benzene ring, and (iii) the MMP-10 inhibition pattern of the compounds paralleled that for MMP-9.

PMID:
18442906
PMCID:
PMC2490768
DOI:
10.1016/j.bmcl.2008.04.035
[Indexed for MEDLINE]
Free PMC Article

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