3-(5-methoxy-1-(3-(dimethylamino)propyl)-1H-indol-3-yl)-1-phenyl-4-(1H-pyrrolo[3,2-b]pyridin-1-yl)-1H-pyrrole-2,5-dione | 1178894-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-(5-methoxy-1-(3-(dimethylamino)propyl)-1H-indol-3-yl)-1-phenyl-4-(1H-pyrrolo[3,2-b]pyridin-1-yl)-1H-pyrrole-2,5-dione
• CAS: 1178894-53-5
• 化学式: C₃₁H₂₉N₅O₃
• 分子量: 519.603
• InChiKey: AAVOJVPPLGGGAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.6
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-(5-methoxy-1-(3-(dimethylamino)propyl)-1H-indol-3-yl)-1-phenyl-4-(1H-pyrrolo[3,2-b]pyridin-1-yl)-1H-pyrrole-2,5-dione 在 ammonium acetate 作用下， 反应 4.0h， 以77.6%的产率得到3-(5-methoxy-1-(3-(dimethylamino)propyl)-1H-indol-3-yl)-4-(1H-pyrrolo[3,2-b]pyridin-1-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 4-azaindolyl-indolyl-maleimides as glycogen synthase kinase-3β (GSK-3β) inhibitors

  摘要：

  A series of novel 4-azaindolyl-indolyl-maleimides were synthesized and evaluated for their GSK-3 beta inhibitory activity. Most compounds exhibited high potency to GSK-3 beta. Among them, compound 7c was the most promising GSK-3 beta inhibitor. Preliminary structure-activity relationships were discussed based on the experimental data obtained and showed that different substituents on the indole ring and side chains at 1-position of indole had varying degrees of influence on the GSK-3 beta inhibitory potency. In a cell-based functional assay, compounds 7c and 15a significantly reduced A beta-induced Tau hyperphosphorylation by inhibiting GSK-3 beta. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.031
• 作为产物：
  描述：

  3-(5-methoxy-1H-indol-3-yl)-1-phenyl-4-(1H-pyrrolo[3,2-b]pyridin-1-yl)-1H-pyrrole-2,5-dione 、 N,N-二甲基-3-氯丙胺 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.0h， 以41.7%的产率得到3-(5-methoxy-1-(3-(dimethylamino)propyl)-1H-indol-3-yl)-1-phenyl-4-(1H-pyrrolo[3,2-b]pyridin-1-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 4-azaindolyl-indolyl-maleimides as glycogen synthase kinase-3β (GSK-3β) inhibitors

  摘要：

  A series of novel 4-azaindolyl-indolyl-maleimides were synthesized and evaluated for their GSK-3 beta inhibitory activity. Most compounds exhibited high potency to GSK-3 beta. Among them, compound 7c was the most promising GSK-3 beta inhibitor. Preliminary structure-activity relationships were discussed based on the experimental data obtained and showed that different substituents on the indole ring and side chains at 1-position of indole had varying degrees of influence on the GSK-3 beta inhibitory potency. In a cell-based functional assay, compounds 7c and 15a significantly reduced A beta-induced Tau hyperphosphorylation by inhibiting GSK-3 beta. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.031