Structure--activity relationships of azasugar-based MMP/ADAM inhibitors

Hideki Moriyama; Takahiro Tsukida; Yoshimasa Inoue; Hirosato Kondo; Kohichiro Yoshino; Shin-ichiro Nishimura

doi:10.1016/s0960-894x(03)00530-4

Structure--activity relationships of azasugar-based MMP/ADAM inhibitors

Bioorg Med Chem Lett. 2003 Aug 18;13(16):2737-40. doi: 10.1016/s0960-894x(03)00530-4.

Authors

Hideki Moriyama¹, Takahiro Tsukida, Yoshimasa Inoue, Hirosato Kondo, Kohichiro Yoshino, Shin-ichiro Nishimura

Affiliation

¹ Japan Bioindustry Association, Hokkaido Collaboration Center, N-21, W-12, Kita-Ku, Sapporo 001-0021 Japan.

PMID: 12873504
DOI: 10.1016/s0960-894x(03)00530-4

Abstract

In order to investigate structure-activity relationships of azasugar series toward metalloproteinases, we synthesized and evaluated several azasugar-based compounds. As a result, it was found that 4-phenoxybenzene derivative 3 having 2R,3R,4R,5S-configurations exhibited most potent inhibitory activities against matrix metalloproteinase-1, -3 and -9 and TACE.

Publication types

Comparative Study
Research Support, Non-U.S. Gov't

MeSH terms

ADAM Proteins
ADAM17 Protein
Aza Compounds / chemical synthesis*
Aza Compounds / pharmacology
Benzoates / chemistry
Drug Design
Gluconates / chemistry*
Kinetics
Lactones
Matrix Metalloproteinase Inhibitors*
Metalloendopeptidases / antagonists & inhibitors*
Phenyl Ethers / chemistry
Protease Inhibitors / chemical synthesis*
Protease Inhibitors / pharmacology
Stereoisomerism
Structure-Activity Relationship

Substances

Aza Compounds
Benzoates
Gluconates
Lactones
Matrix Metalloproteinase Inhibitors
Phenyl Ethers
Protease Inhibitors
4-carboxybiphenyl ether
ADAM Proteins
Metalloendopeptidases
ADAM17 Protein
beta-glucono-1,5-lactone