(1S)-1,5-anhydro-1-(2-methoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol | 1443119-73-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-1,5-anhydro-1-(2-methoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol
• CAS: 1443119-73-0
• 化学式: C₂₆H₂₈O₈
• 分子量: 468.504
• InChiKey: ZAJKKDVQHRYQEL-HFBCXCLPSA-N

反应信息

• 作为反应物：
  描述：

  (1S)-1,5-anhydro-1-(2-methoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以98%的产率得到(1S)-1,5-anhydro-1-{5-[(1-carboxyazulen-2-yl)methyl]-2-methoxyphenyl}-D-glucitol
  参考文献：
  名称：

  Synthesis and biological evaluation of C-glucosides with azulene rings as selective SGLT2 inhibitors for the treatment of type 2 diabetes mellitus: Discovery of YM543

  摘要：

  Here, a series of C-glucosides with azulene rings in the aglycon moiety was synthesized and the inhibitory activities toward hSGLT1 and hSGLT2 were evaluated. Starting from the azulene derivative 7 which had relatively good SGLT2 inhibitory activity, compound 8a which has a 3-[(azulen-2-yl)methyl]phenyl group was identified as a lead compound for further optimization. Introduction of a phenolic hydroxyl group onto the central benzene ring afforded a potent and selective SGLT2 inhibitor 8e, which reduced blood glucose levels in a dose-dependent manner in rodent diabetic models. A mono choline salt of 8e (YM543) was selected as a clinical candidate for use in treating type 2 diabetes mellitus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.067
• 作为产物：
  描述：

  (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-(2-methoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以68%的产率得到(1S)-1,5-anhydro-1-(2-methoxy-5-{[1-(methoxycarbonyl)azulen-2-yl]methyl}phenyl)-D-glucitol
  参考文献：
  名称：

  Synthesis and biological evaluation of C-glucosides with azulene rings as selective SGLT2 inhibitors for the treatment of type 2 diabetes mellitus: Discovery of YM543

  摘要：

  Here, a series of C-glucosides with azulene rings in the aglycon moiety was synthesized and the inhibitory activities toward hSGLT1 and hSGLT2 were evaluated. Starting from the azulene derivative 7 which had relatively good SGLT2 inhibitory activity, compound 8a which has a 3-[(azulen-2-yl)methyl]phenyl group was identified as a lead compound for further optimization. Introduction of a phenolic hydroxyl group onto the central benzene ring afforded a potent and selective SGLT2 inhibitor 8e, which reduced blood glucose levels in a dose-dependent manner in rodent diabetic models. A mono choline salt of 8e (YM543) was selected as a clinical candidate for use in treating type 2 diabetes mellitus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.067