title: Alpha-glucosidase inhibitors with a phthalimide skeleton: structure-activity relationship study.
abstract: Alpha-glucosidase inhibitors with a phthalimide skeleton were prepared. Structure-activity relationship studies indicated a critical role for the hydrophobicity of the substituent at the nitrogen atom of the phthalimide skeleton. Introduction of electron-withdrawing groups, including a nitro group and chlorine, influenced the activity. Optimization studies led us to design 4,5,6,7-tetrachloro-N-phenylphthalimide (CPOP) and its N-phenylalkyl derivatives. CP0P and 4,5,6,7-tetrachloro-N-(4-phenylbutyl)phthalimide (CP4P) proved to be more potent alpha-glucosidase inhibitors than the known inhibitor 1-deoxynojirimycin.
authors.affiliation: Institute of Molecular and Cellular Biosciences, University of Tokyo, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Takahashi
authors.forename: S
authors.initials: S
authors.lastname: Sou
authors.forename: R
authors.initials: R
authors.lastname: Yamasaki
authors.forename: M
authors.initials: M
authors.lastname: Sodeoka
authors.forename: Y
authors.initials: Y
authors.lastname: Hashimoto
mesh_terms: D000478:Alkylation; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D065089:Glycoside Hydrolase Inhibitors; D009682:Magnetic Resonance Spectroscopy; D010797:Phthalimides / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D010797:Phthalimides