(S)-3-cyclohexyl-2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)propanoic acid | 1416811-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-3-cyclohexyl-2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)propanoic acid
• 英文别名: (2S)-3-cyclohexyl-2-(5,6-dichloro-1,3-dioxoisoindol-2-yl)propanoic acid
• CAS: 1416811-70-5
• 化学式: C₁₇H₁₇Cl₂NO₄
• 分子量: 370.232
• InChiKey: VWJLQHGAIYZBNS-AWEZNQCLSA-N

物化性质

• 沸点：
  559.0±50.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-cyclohexyl-2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)propanoic acid 在 溶剂黄146 、 锌 作用下， 以71%的产率得到(S)-3-cyclohexyl-2-(5,6-dichloro-1-oxoisoindolin-2-yl)propanoic acid
  参考文献：
  名称：

  Discovery of novel dual-action antidiabetic agents that inhibit glycogen phosphorylase and activate glucokinase

  摘要：

  Dual-target-directed agents simultaneously inhibiting glycogen phosphorylase (GP) and activating glucokinase (GK) could decelerate the inflow of glucose from glycogenolysis and accelerate the outflow of glucose in the liver, therefore allow for a better control over hyperglycaemia in a synergetic manner. A series of hybrid compounds were designed by structure-assisted and ligand-based strategies. In vitro bioassays found two novel compounds (1j, 6g) worthy of further optimization on balance of dual action to GP and GK. In addition, for single-target activity, two compounds exhibited more potent GP inhibitory activity and four compounds showed better GK activation than their corresponding references. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.020
• 作为产物：
  描述：

  4,5-二氯苯二甲酸 在 乙酸酐 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 (S)-3-cyclohexyl-2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)propanoic acid
  参考文献：
  名称：

  Discovery of novel dual-action antidiabetic agents that inhibit glycogen phosphorylase and activate glucokinase

  摘要：

  Dual-target-directed agents simultaneously inhibiting glycogen phosphorylase (GP) and activating glucokinase (GK) could decelerate the inflow of glucose from glycogenolysis and accelerate the outflow of glucose in the liver, therefore allow for a better control over hyperglycaemia in a synergetic manner. A series of hybrid compounds were designed by structure-assisted and ligand-based strategies. In vitro bioassays found two novel compounds (1j, 6g) worthy of further optimization on balance of dual action to GP and GK. In addition, for single-target activity, two compounds exhibited more potent GP inhibitory activity and four compounds showed better GK activation than their corresponding references. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.020

文献信息

• Discovery of novel dual-action antidiabetic agents that inhibit glycogen phosphorylase and activate glucokinase
  作者：Lei Zhang、Xiaojie Chen、Jun Liu、Qingzhang Zhu、Ying Leng、Xiaomin Luo、Hualiang Jiang、Hong Liu

  DOI：10.1016/j.ejmech.2012.06.020

  日期：2012.12

  Dual-target-directed agents simultaneously inhibiting glycogen phosphorylase (GP) and activating glucokinase (GK) could decelerate the inflow of glucose from glycogenolysis and accelerate the outflow of glucose in the liver, therefore allow for a better control over hyperglycaemia in a synergetic manner. A series of hybrid compounds were designed by structure-assisted and ligand-based strategies. In vitro bioassays found two novel compounds (1j, 6g) worthy of further optimization on balance of dual action to GP and GK. In addition, for single-target activity, two compounds exhibited more potent GP inhibitory activity and four compounds showed better GK activation than their corresponding references. (C) 2012 Elsevier Masson SAS. All rights reserved.