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http://dx.doi.org/10.5012/bkcs.2010.31.11.3359

Microwave-Accelerated Click Chemistry: Expeditious Synthesis of Novel Triazole-linked Salicylic β-D-O-Glycosides with PTP1B Inhibitory Activity  

Yang, Jin-Wei (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology)
Li, Cui (School of Pharmacy, East China University of Science and Technology)
He, Xiao-Peng (School of Pharmacy, East China University of Science and Technology)
Zhao, Hong (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology)
Gao, Li-Xin (National Center for Drug Screening, Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences)
Zhang, Wei (National Center for Drug Screening, Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences)
Shi, Xiao-Xin (School of Pharmacy, East China University of Science and Technology)
Tang, Yun (School of Pharmacy, East China University of Science and Technology)
Li, Jia (National Center for Drug Screening, Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences)
Chen, Guo-Rong (Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology)
Publication Information
Bulletin of the Korean Chemical Society / v.31, no.11, 2010 , pp. 3359-3365 More about this Journal
Abstract
The incorporation of microwave irradiation with the prevalent "click chemistry" is currently of considerable synthetic interest. We describe here the introduction of such laboratorial shortcut into carbohydrate-based drug discovery, resulting in the rapid formation of a series of triazole-linked salicylic $\beta$-D-O-glycosides with biological activities. All "clicked" products were achieved in excellent yields ($\approx$ 90%) within only a quarter. In addition, based on the structural characteristics of the afforded glycomimetics, their inhibitory activities were evaluated toward protein tyrosine phosphatases 1B (PTP1B) and a panel of homologous protein tyrosine phosphatases (PTPs). Docking simulation was also conducted to plausibly propose binding modes of this glycosyl salicylate series with the enzymatic target.
Keywords
Click chemistry; Microwave irradiation; Carbohydrate-based drug discovery; PTP1B inhibitor; Docking simulation;
Citations & Related Records
Times Cited By KSCI : 3  (Citation Analysis)
Times Cited By Web Of Science : 8  (Related Records In Web of Science)
Times Cited By SCOPUS : 9
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