Synthesis and evaluation of ent-Conduramine C-1 derivatives as α-glucosidase inhibitors via CSI-mediated amination reaction

Concise synthesis of ent-conduramine C-1 and its derivatives has been achieved by using commercially available D-ribose. The key steps in the synthesis are regioselective and diastereoselective amination of polybenzyl ethers by chlorosulfonyl isocyanate (CSI), chelation-controlled carbonyl addition, and intramolecular olefin metathesis. All of the synthesized compounds were evaluated for inhibitory activity against alpha-glucosidase. The derivatives 18 (IC50 = 0.65 +/- 0.03 mM) and 19 (IC50 = 0.26 +/- 0.01 mM) were identified to be more potent than well-known alpha-glucosidase inhibitor acarbose (IC50 = 1.05 +/- 0.17 mM) as a positive control.

Automated summary

A concise synthesis of ent-conduramine C-1 and its derivatives has been achieved using commercially available D-ribose. The key steps in the synthesis involved regioselective and diastereoselective amination, chelation-controlled carbonyl addition, and intramolecular olefin metathesis. The synthesized compounds were evaluated for their inhibitory activity against alpha-glucosidase, with derivatives 18 and 19 showing stronger inhibition than acarbose.