Synthesis and Biological Evaluation of New Dihydrofuro[3,2-<i>b</i>]piperidine Derivatives as Potent <i>α</i>-Glucosidase Inhibitors

Abstract

Inhibition of glycoside hydrolases has widespread application in the treatment of diabetes. Based on our previous findings, a series of dihydrofuro[3,2-b]piperidine derivatives was designed and synthesized from D- and L-arabinose. Compounds 32 (IC50 = 0.07 μM) and 28 (IC50 = 0.5 μM) showed significantly stronger inhibitory potency against α-glucosidase than positive control acarbose. The study of the structure–activity relationship of these compounds provides a new clue for the development of new α-glucosidase inhibitors.

Keywords

• dihydrofuro[3,2-<i>b</i>]piperidine
• iminosugar
• <i>C</i>-glycosides
• glucosidase
• inhibitors