Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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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)
  • Received : 2010.08.02
  • Accepted : 2010.09.15
  • Published : 2010.11.20
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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.

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