Bulletin of the Korean Chemical Society

  • 제31권11호
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  • Pages.3359-3365
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  • 2010
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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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)
  • 투고 : 2010.08.02
  • 심사 : 2010.09.15
  • 발행 : 2010.11.20
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초록

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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피인용 문헌

  1. -Glycoside Hybrids via Click Chemistry as Novel PTP1B Inhibitors vol.29, pp.6, 2011, https://doi.org/10.1002/cjoc.201190228
  2. Microwave-assisted construction of triazole-linked amino acid–glucoside conjugates as novel PTP1B inhibitors vol.35, pp.3, 2011, https://doi.org/10.1039/c0nj00835d
  3. ChemInform Abstract: Microwave-Accelerated Click Chemistry: Expeditious Synthesis of Novel Triazole-Linked Salicylic β-D-O-Glycosides with PTP1B Inhibitory Activity. vol.42, pp.13, 2011, https://doi.org/10.1002/chin.201113200
  4. Bidentate Inhibitors of Protein Tyrosine Phosphatases vol.20, pp.14, 2014, https://doi.org/10.1089/ars.2013.5710
  5. Monosaccharide as a Central Scaffold Toward the Construction of Salicylate-Based Bidentate PTP1B Inhibitors via Click Chemistry vol.32, pp.3, 2010, https://doi.org/10.5012/bkcs.2011.32.3.1000
  6. Creation of 3,4-bis-triazolocoumarin–sugar conjugates via flourogenic dual click chemistry and their quenching specificity with silver(I) in aqueous media vol.67, pp.19, 2010, https://doi.org/10.1016/j.tet.2011.03.068
  7. Disclosing the distinct interfacial behaviors of structurally and configurationally diverse triazologlycolipids vol.346, pp.11, 2010, https://doi.org/10.1016/j.carres.2011.04.038
  8. Click to a focused library of benzyl 6-triazolo(hydroxy)benzoic glucosides: Novel construction of PTP1B inhibitors on a sugar scaffold vol.46, pp.9, 2010, https://doi.org/10.1016/j.ejmech.2011.06.025
  9. CuAAC Click Chemistry Accelerates the Discovery of Novel Chemical Scaffolds as Promising Protein Tyrosine Phosphatases Inhibitors vol.19, pp.15, 2010, https://doi.org/10.2174/092986712800269245
  10. Multifunctional Molecular Therapeutic Agent for Targeted and Controlled Dual Chemo- and Photodynamic Therapy vol.63, pp.15, 2010, https://doi.org/10.1021/acs.jmedchem.0c00893