A Facile Synthesis of Pyrrolidine-Based Iminosugars as Potential Alpha-Glucosidase Inhibitors

Abstract

A multifaceted approach comprising MCR (multicomponent reaction), amination and stereoselective reduction reactions was used to synthesize new pyrrolidine-based iminosugars. The key step of this strategy involves the contruction of a highly functionalised pyrroldine ring skeleton through MCR approach. Subsequently, amination and reduction reactions to the ring skeleton provide a quick access to new pyrrolidine-based imino sugars. The iminosugars were then tested against alpha glucosidase activity in which one compound (4-((4-methoxyphenyl)amino)pyrrolidin-3-ol), was found to be the most potent at low dosage.

rac-Ethyl rel-(2R,3R,4S)-4-hydroxy-1,2-dimethyl-5-oxopyrrolidine-3-carboxylate

“…During the course of our study towards pyrrolidine-based iminosugars, we have synthesized the title compound by reduction of 2,3-dioxopyrrolidine (Bacho et al, 2020;Abdul Rashid et al, 2020). The starting material, 2,3-dioxopyrrolidine, was initially prepared via a multicomponent reaction, according to a previously reported procedure (Mohammat et al, 2009(Mohammat et al, , 2011.…”