Synthesis ofN-phenylphthalimide Derivatives as α-Glucosidase Inhibitors

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.

Inhibition of monoamine oxidase by C5-substituted phthalimide analogues

“…31 The N-substituted phthalimide analogues 6a-c were, in turn, prepared by reacting phthalic anhydride (8) with the appropriate amine in glacial acetic acid (Scheme 2). 32 In each instance, the structures and purities of the target compounds were verified by 1 H NMR, 13 C NMR, mass spectrometry and HPLC analysis as cited in the experimental section.…”

“…procedure. 32 A mixture of the appropriate amine (12 mmol) and phthalic anhydride (8; 10 mmol) were heated under reflux in 1 M acetic acid (20 mL) for 5 h. The reaction was allowed to cool to room temperature, water (100 mL) was added and the precipitated product was collected by filtration. The target N-substituted phthalimide analogues were recrystallized from 95% ethanol.…”

A series of cinnamic acid derivatives and their inhibitory activity on intestinal α-glucosidase

“…The assessment of intestinal -glucosidase inhibitory activity was slightly modified, according to a previous method 11 . Briefly, 100 mg of rat intestinal acetone powder was homogenized in 3 mL of 0.9% NaCl solution.…”

Synthesis of PPAR-γ Activators Inspired by the Marine Natural Product, Paecilocin A

“…N -substituted phthalimides can be prepared by heating phthalic anhydride with various N -containing reagents [19]. In the present study, this was performed by treating phthalic anhydrides ( 1 , 2 ) with various amines in the presence of acetic acid to generate corresponding N -substituted phthalimides (Scheme 1).…”