Synthesis and biological activity of glycosyl-1H-1,2,3-triazoles

被引：40
|
作者：
Slamova, Kristyna [1 ]
Marhol, Petr [1 ]
Bezouska, Karel [1 ,3 ]
Lindkvist, Lise [2 ]
Hansen, Signe G. [2 ]
Kren, Vladimir [1 ]
Jensen, Henrik H. [2 ]
机构：
[1] Acad Sci Czech Republ, Inst Microbiol, Ctr Biocatalysis & Biotransformat, CZ-14220 Prague, Czech Republic
[2] Aarhus Univ, Dept Chem, DK-8000 Aarhus C, Denmark
[3] Charles Univ Prague, Fac Sci, Dept Biochem, CZ-12840 Prague 2, Czech Republic
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 14期
关键词：
Glycosidase inhibition; beta-N-Acetylhexosaminidase; N-Glycoside; NK cell; GLYCOSYL AZIDES;
D O I：
10.1016/j.bmcl.2010.04.151
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Glycosyl 1,2,3-triazoles with alpha-D-gluco, beta-D-gluco, alpha-D-galacto, beta-D-galacto and beta-2-acetamido-2-deoxygluco (GlcNAc) stereochemistry were prepared by reaction of the corresponding azides with vinyl acetate under microwave irradiation. The deprotected glucosyl and galactosyl triazoles did not display inhibitory activity against the tested glycosidases at 1 mM. Of the four fungal glycosidases evaluated, GlcNAc-triazole was found to be hydrolyzed by Talaromyces flavus CCF 2686 beta-N-acetylhexosaminidase. beta-GlcNAc-triazole was furthermore established to act as a strong ligand of rat and human natural killer cell activating receptors. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4263 / 4265
页数：3
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