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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 11
BKCSDE 31(11)
November 20, 2010 

 
Title
Microwave-Accelerated Click Chemistry: Expeditious Synthesis of Novel Triazole-linked Salicylic β-D-O-Glycosides with PTP1B Inhibitory Activity
Author
Jin Wei Yang, Cui Li, Xiao Peng He, Hong Zhao, Li Xin Gao, Wei Zhang, Xiao Xin Shi, Yun Tang, Jia Li*, Guo Rong Chen*
Keywords
Click chemistry, Microwave irradiation, Carbohydrate-based drug discovery, PTP1B inhibitor, Docking simulation
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 β-D-O-glycosides with biological activities. All “clicked” products were achieved in excellent yields (? 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.
Page
3359 - 3365
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