Synthesis of N-phenylphthalimide derivatives as alpha-glucosidase inhibitors.
Sixteen N-phenylphthalimide derivatives were synthesized and their ability to inhibit alpha-glucosidase was investigated. N-(2,4-dinitrophenyl)phthalimide was a potent inhibitor of yeast alpha-glucosidase (IC50; 0.158 +/- 0.005 mM) and maltase (IC50; 0.051 +/- 0.008 mM), whereas it did not inhibit sucrase. From a Lineweaver-Burk plot of alpha-glucosidase kinetics, N-(2,4-dichlorophenyl)phthalimide was found to be a competitive inhibitor of yeast alpha-glucosidase. These results indicate that N-(2,4-dinitrophenyl)phthalimide could be a representative of a new group of alpha-glucosidase inhibitors.
Pluempanupat
Wanchai
W
Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
Adisakwattana
Sirichai
S
Yibchok-Anun
Sirintorn
S
Chavasiri
Warinthorn
W
D000818:Animals; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D065089:Glycoside Hydrolase Inhibitors; D010797:Phthalimides / Q000138:chemical synthesis* / Q000737:chemistry; D051381:Rats; D013329:Structure-Activity Relationship
D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D010797:Phthalimides