2-(1-(3-morpholinopropyl)-1H-indol-3-yl)acetamide | 1178894-75-1

• 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: 2-(1-(3-morpholinopropyl)-1H-indol-3-yl)acetamide
• 英文别名: 2-[1-(3-Morpholin-4-ylpropyl)indol-3-yl]acetamide；2-[1-(3-morpholin-4-ylpropyl)indol-3-yl]acetamide
• CAS: 1178894-75-1
• 化学式: C₁₇H₂₃N₃O₂
• 分子量: 301.389
• InChiKey: IYXIYAFWTBWORT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  60.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-2-oxoacetate 、 2-(1-(3-morpholinopropyl)-1H-indol-3-yl)acetamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以11.2%的产率得到3-(1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-4-(1-(3-morpholinopropyl)-1H-indol-3-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：

  N-(3-氯丙基)吗啉 、 3-吲哚乙酰胺 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2-(1-(3-morpholinopropyl)-1H-indol-3-yl)acetamide
  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

文献信息

• Synthesis and biological evaluation of novel 4-azaindolyl-indolyl-maleimides as glycogen synthase kinase-3β (GSK-3β) inhibitors
  作者：Qing Ye、Guiqing Xu、Dan Lv、Zhe Cheng、Jia Li、Yongzhou Hu

  DOI：10.1016/j.bmc.2009.05.031

  日期：2009.7

  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.