Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (06): 849-859. Previous Articles     Next Articles

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  1. 1曲阜师范大学化学与化工学院 曲阜 273165)
    (2天津药物研究院分子设计与药物发现天津市重点实验室 天津 300193
  • 收稿日期:2009-08-16 修回日期:2009-10-10 发布日期:2010-01-15
  • 通讯作者: 赵桂龙
  • 基金资助:


Design, Synthesis and Anti-diabetic Activity of Thiadiazole-Based Thioglycosides as SGLT2 Inhibitors

Wang Zhifeng1 Zhao Guilong*,2 Liu Wei2 Wang Yuli2 Shao Hua2 Xu Weiren2 Tian Laijin*,1   

  1. 1 School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165)
    (2 Tianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193
  • Received:2009-08-16 Revised:2009-10-10 Published:2010-01-15

22 thioglycosides with novel structure were designed and synthesized from 5-substituded phenyloxymethyl-2-mercapto-1,3,4-thiadiazole and tetra-O-acetyl-α-glycopyranosyl bromides in the presence of phase transfer catalysis (BnEt3NBr) at room temperature. These compounds were characterized by IR, 1H NMR, 13C NMR, and HR-ESI-MS techniques. Bioactivity of decreasing blood glucose was performed through in vivo by oral glucose tolerance test (OGTT) in mice. In addition, preliminary pharmacological test showed that compound 9Ah was more potent than positive control gliclazide, while compounds 9Aa and 9Bi were comparable to gliclazide in potency.

Key words: thiadiazole, thioglycoside, SGLT2 inhibitor, synthesis, anti-hyperglycemic activity