Novel alpha-glucosidase inhibitors with a tetrachlorophthalimide skeleton

S Sou; S Mayumi; H Takahashi; R Yamasaki; S Kadoya; M Sodeoka; Y Hashimoto

doi:10.1016/s0960-894x(00)00161-x

Novel alpha-glucosidase inhibitors with a tetrachlorophthalimide skeleton

Bioorg Med Chem Lett. 2000 May 15;10(10):1081-4. doi: 10.1016/s0960-894x(00)00161-x.

Authors

S Sou¹, S Mayumi, H Takahashi, R Yamasaki, S Kadoya, M Sodeoka, Y Hashimoto

Affiliation

¹ Institute of Molecular and Cellular Biosciences, University of Tokyo, Japan.

PMID: 10843222
DOI: 10.1016/s0960-894x(00)00161-x

Abstract

Novel alpha-glucosidase inhibitors with a tetrachlorophthalimide skeleton were prepared and their structure-activity relationships were analyzed. Among them, N-phenyl-4,5,6,7-tetrachlorophthalimide (CPOP: 2) and N-(4-phenylbutyl)-4,5,6,7-tetrachlorophthalimide (CP4P: 6) showed very potent inhibitory activity, being more potent than 1-deoxynojirimycin (dNM: 1). Mechanistic studies revealed that CPOP (2) and CP4P (6) inhibit alpha-glucosidase non-competitively and competitively, respectively.

Publication types

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

MeSH terms

1-Deoxynojirimycin / chemistry
1-Deoxynojirimycin / pharmacology
Binding Sites
Catalytic Domain
Enzyme Inhibitors / chemistry*
Enzyme Inhibitors / metabolism
Enzyme Inhibitors / pharmacology*
Glycoside Hydrolase Inhibitors*
Inhibitory Concentration 50
Phthalimides / chemistry*
Phthalimides / metabolism
Phthalimides / pharmacology*
Structure-Activity Relationship
alpha-Glucosidases / metabolism

Substances

Enzyme Inhibitors
Glycoside Hydrolase Inhibitors
N-(4-phenylbutyl)-4,5,6,7-tetrachlorophthalimide
N-phenyl-4,5,6,7-tetrachlorophthalimide
Phthalimides
1-Deoxynojirimycin
alpha-Glucosidases