期刊
CARBOHYDRATE RESEARCH
卷 346, 期 1, 页码 140-145出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2010.10.023
关键词
alpha-Ketocarboxylic acid; Glycoconjugate; Click reaction; PTP1B inhibitor
资金
- National Natural Science Foundation of China [20876045]
- National Science & Technology Major Project of China 'Key New Drug Creation and Manufacturing Program [2009ZX09302-001]
- Shanghai Science and Technology Community [10410702700, 08DZ2291300]
- Chinese Academy of Sciences [KSCX2-YW-R-168]
- French Embassy in Beijing, China
The synthesis of triazole-linked glycosyl acetophenone, benzoic acid, and alpha-ketocarboxylic acid derivatives was readily achieved via Cu(I)-catalyzed azide-alkyne cycloaddition ('click' reaction) in excellent yields of 93-97%. Among the synthesized glycoconjugates, the triazolyl alpha-ketocarboxylic acids were identified as the most potent protein tyrosine phosphatase 1B (FTP1B) inhibitors with micromole-ranged IC50 values and moderate-to-good selectivity over a panel of homologous PTPs including TCPTP (4.6-fold), LAR (>30-fold), SHP-1 (>30-fold) and SHP-2 (>30-fold). Moreover, a docking simulation was conducted to propose a plausible binding mode of the glucosyl alpha-ketocarboxylic acid triazole with the enzymatic target. (C) 2010 Elsevier Ltd. All rights reserved.
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