(2S,3S,4R,5S,6S)-2-(4-methoxy-3-(((1s,4S)-4-propylcyclohexyl)methyl)phenyl)-6-((phenylthio)methyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1431771-91-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5S,6S)-2-(4-methoxy-3-(((1s,4S)-4-propylcyclohexyl)methyl)phenyl)-6-((phenylthio)methyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1431771-91-3
• 化学式: C₃₅H₄₆O₈S
• 分子量: 626.811
• InChiKey: YGPAGHYJFRXMRJ-RHAQRITMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S,6S)-2-(4-methoxy-3-(((1s,4S)-4-propylcyclohexyl)methyl)phenyl)-6-((phenylthio)methyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 sodium 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (2S,3R,4R,5S,6S)-2-(4-methoxy-3-(((1s,4S)-4-propylcyclohexyl)methyl)phenyl)-6-((phenylthio)methyl)tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Design, synthesis and biological activity of cyclohexane-bearing C-glucoside derivatives as SGLT2 inhibitors

  摘要：

  Seven cyclohexane-bearing C-glucoside derivatives (7, 9, 12, 13 and 17-19) were designed and synthesized as SGLT2 inhibitors starting from a potent SGLT2 inhibitor we discovered in earlier work, (1S)-1-deoxy-1-[4-methoxy-3-(trans-n-propylcyclohexyl)methylphenyl]-D-glucose (1). The in vitro and in vivo biological activities were evaluated by hSGLT2/hSGLT1 inhibition and urinary glucose excretion (UGE), respectively. Among the synthesized compounds 12, the 6-deoxy derivative of 1 was the most active and selective SGLT2 inhibitor (IC50 = 1.4 nmol/L against hSGLT2; selectivity = 1576). Compound 12 was a potent SGLT2 inhibitor, which could induce more urinary glucose than 1 and dapagliflozin in UGE. (C) 2013 Gui-Long Zhao, Jian-Wu Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.03.026
• 作为产物：
  描述：

  (1S)-1-deoxy-1-[4-methoxy-3-(trans-n-propylcyclohexyl)methylphenyl]-D-glucopyranose 在 咪唑 、 4-二甲氨基吡啶 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3S,4R,5S,6S)-2-(4-methoxy-3-(((1s,4S)-4-propylcyclohexyl)methyl)phenyl)-6-((phenylthio)methyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Design, synthesis and biological activity of cyclohexane-bearing C-glucoside derivatives as SGLT2 inhibitors

  摘要：

  Seven cyclohexane-bearing C-glucoside derivatives (7, 9, 12, 13 and 17-19) were designed and synthesized as SGLT2 inhibitors starting from a potent SGLT2 inhibitor we discovered in earlier work, (1S)-1-deoxy-1-[4-methoxy-3-(trans-n-propylcyclohexyl)methylphenyl]-D-glucose (1). The in vitro and in vivo biological activities were evaluated by hSGLT2/hSGLT1 inhibition and urinary glucose excretion (UGE), respectively. Among the synthesized compounds 12, the 6-deoxy derivative of 1 was the most active and selective SGLT2 inhibitor (IC50 = 1.4 nmol/L against hSGLT2; selectivity = 1576). Compound 12 was a potent SGLT2 inhibitor, which could induce more urinary glucose than 1 and dapagliflozin in UGE. (C) 2013 Gui-Long Zhao, Jian-Wu Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.03.026