Synthesis of N-phenylphthalimide derivatives as alpha-glucosidase inhibitors

Wanchai Pluempanupat; Sirichai Adisakwattana; Sirintorn Yibchok-Anun; Warinthorn Chavasiri

doi:10.1007/BF02977317

Synthesis of N-phenylphthalimide derivatives as alpha-glucosidase inhibitors

Arch Pharm Res. 2007 Dec;30(12):1501-6. doi: 10.1007/BF02977317.

Authors

Wanchai Pluempanupat¹, Sirichai Adisakwattana, Sirintorn Yibchok-Anun, Warinthorn Chavasiri

Affiliation

¹ Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.

PMID: 18254235
DOI: 10.1007/BF02977317

Abstract

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.

Publication types

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

MeSH terms

Animals
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Glycoside Hydrolase Inhibitors*
Phthalimides / chemical synthesis*
Phthalimides / chemistry
Rats
Structure-Activity Relationship

Substances

Enzyme Inhibitors
Glycoside Hydrolase Inhibitors
Phthalimides