Novel alpha-glucosidase inhibitors with a tetrachlorophthalimide skeleton.
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.
Sou
S
S
Institute of Molecular and Cellular Biosciences, University of Tokyo, Japan.
Mayumi
S
S
Takahashi
H
H
Yamasaki
R
R
Kadoya
S
S
Sodeoka
M
M
Hashimoto
Y
Y
D017485:1-Deoxynojirimycin / Q000737:chemistry / Q000494:pharmacology; D001665:Binding Sites; D020134:Catalytic Domain; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D065089:Glycoside Hydrolase Inhibitors; D020128:Inhibitory Concentration 50; D010797:Phthalimides / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D000520:alpha-Glucosidases / Q000378:metabolism
D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; C413733:N-(4-phenylbutyl)-4,5,6,7-tetrachlorophthalimide; C413732:N-phenyl-4,5,6,7-tetrachlorophthalimide; D010797:Phthalimides; D017485:1-Deoxynojirimycin; D000520:alpha-Glucosidases