methyl 2-[[(2S)-3-cyclohexyl-2-(5,6-dichloro-3-oxo-1H-isoindol-2-yl)propanoyl]amino]-1,3-thiazole-5-carboxylate | 1416810-70-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: methyl 2-[[(2S)-3-cyclohexyl-2-(5,6-dichloro-3-oxo-1H-isoindol-2-yl)propanoyl]amino]-1,3-thiazole-5-carboxylate
• CAS: 1416810-70-2
• 化学式: C₂₂H₂₃Cl₂N₃O₄S
• 分子量: 496.414
• InChiKey: SRZAOXLBFYZMRE-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[[(2S)-3-cyclohexyl-2-(5,6-dichloro-3-oxo-1H-isoindol-2-yl)propanoyl]amino]-1,3-thiazole-5-carboxylate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到(2S)-3-cyclohexyl-2-(5,6-dichloro-3-oxo-1H-isoindol-2-yl)-N-[5-(hydroxymethyl)-1,3-thiazol-2-yl]propanamide
  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：

  4,5-二氯邻苯二甲酸酐 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 锌 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 methyl 2-[[(2S)-3-cyclohexyl-2-(5,6-dichloro-3-oxo-1H-isoindol-2-yl)propanoyl]amino]-1,3-thiazole-5-carboxylate
  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