期刊
CARBOHYDRATE RESEARCH
卷 399, 期 -, 页码 38-48出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2014.05.020
关键词
Xylose derivative; Benzimidazole; 1,2,4-Triazole; Spiro-isoxazoline; Spiro-1,4,2-oxathiazole; Glycogen phosphorylase inhibitor
资金
- Hungarian Scientific Research Fund [OTKA PD105808, K109450]
- European Union
- European Social Fund
- Hungarian Academy of Sciences
- University of Debrecen [5N5X 1IJ0 KUDT 320]
- Magyary Zoltan Scholarship [TAMOP-4.2.4.A/2-11/1-2012-0001]
- [BAROSS REG_EA_09-1-2009-0028 (LCMS_TAN)]
- [TAMOP-4.2.1./B-09/1/KONV-2010-0007]
- [TAMOP-4.2.2./A-11/1/KONV-2012-0025]
New derivatives of D-xylose with aglycons of the most efficient glucose derived inhibitors of glycogen phosphorylase were synthesized to explore the specificity of the enzyme towards the structure of the sugar part of the molecules. Thus, 2-(beta-D-xylopyranosyl) benzimidazole and 3-substituted-5-(beta-D-xylopyranosyl)1,2,4-triazoles were obtained in multistep procedures from O-perbenzoylated b-D-xylopyranosyl cyanide. Cycloadditions of nitrile-oxides and O-peracetylated exo-xylal obtained from the corresponding beta-D-xylopyranosyl cyanide furnished xylopyranosylidene-spiro-isoxazoline derivatives. Oxidative ring closure of O-peracetylated beta-D-xylopyranosyl-thiohydroximates prepared from 1-thio-beta-D-xylopyranose and nitrile-oxides gave xylopyranosylidene-spiro-oxathiazoles. The fully deprotected test compounds were assayed against rabbit muscle glycogen phosphorylase b to show moderate inhibition for 3-(2-naphthyl)-5-(beta-D-xylopyranosyl)-1,2,4-triazole (IC50 = 0.9 mM) only. (C) 2014 Elsevier Ltd. All rights reserved.
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