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International Research Journal of Pure and Applied Chemistry

International Research Journal of Pure and Applied Chemistry, ISSN: 2231-3443,Vol.: 14, Issue.: 2

 

Short Research Article

 

Simple Synthesis of Sulfonyl Amidine-Containing Glucosidase Inhibitors by a Chemoselective Coupling Reaction Between D-Gluconothiolactam and Sulfonyl Azides

 

 

Muhammad Aswad1,2, Junya Chiba1*, Takenori Tomohiro1 and Yasumaru Hatanaka1

1Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.

2Faculty of Pharmacy, Hasanuddin University, Makassar, South Sulawesi 90245, Indonesia.

 

Abstracts

 

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 α- and β-glucosidases with Ki values of 13.9 and 8.2 μM, respectively, resulting that gluconoamidinylsulfones would be expected to entry in a new class of promising potential inhibitors toward various glycan-processing enzymes.

 

Keywords :

Inhibitor; glycosidase; iminosugar; coupling reaction; one-step synthesis; thioamide; sulfonyl azide; gluconoamidinylsulfone.

 

Full Article - PDF    Page 1-8    Article Metrics

 

DOI : 10.9734/IRJPAC/2017/34259

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