Simple Synthesis of Sulfonyl Amidine-Containing Glucosidase Inhibitors by a Chemoselective Coupling Reaction Between D-Gluconothiolactam and Sulfonyl Azides
Muhammad Aswad, Junya Chiba, Takenori Tomohiro, Yasumaru Hatanaka
International Research Journal of Pure and Applied Chemistry · pp. 1–8 · Published 15 Jun 2017
10.9734/IRJPAC/2017/34259Abstract
In this report, we describe a simple synthesis of gluconoamidinylsulfones as a new class of potential inhibitors toward glycan processing enzymes. Gluconoamidinylsulfones have a glucose-based sulfonyl amidine skeleton, thus would form a distorted half-chair conformation with positive charge, which is analogous to transition state in the enzymatic process. A chemoselective coupling reaction between thioamide and sulfonyl azide enabled one-step synthesis of the iminosugar derivatives from commercially available D-gluconothiolactam in a protection-free manner. The phenyl-substituted gluconoamidinylsulfone displayed high inhibitory ability toward a- and b-glucosidases with Ki values of 13.9 and 8.2 mM, respectively, resulting that gluconoamidinylsulfones would be expected to entry in a new class of promising potential inhibitors toward various glycan-processing enzymes.
Cited by 1
Muhammad Aswad, Umbi Safariah, Risfah Yulianty · AIP Conference Proceedings · 2022
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