Chemical synthesis and preliminary biological evaluation of C-6-O-methyl-1-deoxynojirimycin as a potent α-glucosidase inhibitor

Abstract

A facile and efficient synthesis of 6-O-methyl-1-deoxynojirimycin 4 from commercially available methyl α-D-glucopyranoside in 10 steps and 25% overall yield was reported. The synthetic strategy was based on the regioselective protection/deprotection at 6-O-position and cyclization as the main reaction steps. Compound 4 was evaluated for its inhibitory effect (IC₅₀) on α-glucosidase using an in vitro assay. It showed improved inhibitory activity compared to 1-deoxynojirimycin and acarbose.

Keywords:

• α-Glucosidase
• Chemical synthesis
• IC50
• Inhibitor
• 1-deoxynojirimycin

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was supported by grants from the prospective joint project of Production, Education and Research in Jiangsu Province, PR China [Grant No. KS03008].