Synthesis and biological activity of selective azasugar-based TACE inhibitors

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

doi:10.1016/j.bmcl.2003.12.091

Synthesis and biological activity of selective azasugar-based TACE inhibitors

Bioorg Med Chem Lett. 2004 Mar 22;14(6):1569-72. doi: 10.1016/j.bmcl.2003.12.091.

Authors

Takahiro Tsukida¹, Hideki Moriyama, Yoshimasa Inoue, Hirosato Kondo, Kohichiro Yoshino, Shin-Ichiro Nishimura

Affiliation

¹ R&D Laboratories, Nippon Organon K.K., 1-5-90, Tomobuchi-cho, Miyakojima-ku, Osaka 534-0016, Japan. takiro.tsukida@shionogi.co.jp

PMID: 15006405
DOI: 10.1016/j.bmcl.2003.12.091

Abstract

A series of azasugar-based hydroxamic acid derivatives bearing 2R,3R,4R,5R-configuration is described. Compound 4c with 4,5-O-acetonide group showed excellent in vitro potency against TACE, with high selectivity over MMP-1 and moderate selectivity over MMP-3 and MMP-9.

Publication types

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

MeSH terms

ADAM Proteins
ADAM17 Protein
Aza Compounds / chemical synthesis*
Aza Compounds / metabolism
Humans
Metalloendopeptidases / antagonists & inhibitors*
Metalloendopeptidases / metabolism
Protease Inhibitors / chemical synthesis*
Protease Inhibitors / metabolism
Sugar Acids / chemical synthesis*
Sugar Acids / metabolism

Substances

Aza Compounds
Protease Inhibitors
Sugar Acids
ADAM Proteins
Metalloendopeptidases
ADAM17 Protein
ADAM17 protein, human