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.