Design, synthesis and evaluation of novel azasugar-based MMP/ADAM inhibitors

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

doi:10.1016/s0960-894x(03)00531-6

Design, synthesis and evaluation of novel azasugar-based MMP/ADAM inhibitors

Bioorg Med Chem Lett. 2003 Aug 18;13(16):2741-4. doi: 10.1016/s0960-894x(03)00531-6.

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: 12873505
DOI: 10.1016/s0960-894x(03)00531-6

Abstract

In order to verify whether azasugar would be a useful scaffold for inhibitory activity against metalloproteinases, we synthesized some azasugar-based compounds. As a result, it is clarified that azasugar moiety could function as successful inhibitor of matrix metalloproteinase-1, -3 and -9 and TACE.

MeSH terms

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

Substances

Aza Compounds
Gluconates
Lactones
Matrix Metalloproteinase Inhibitors
Protease Inhibitors
Sulfonamides
ADAM Proteins
Metalloendopeptidases
ADAM17 Protein
Zinc
beta-glucono-1,5-lactone