(4-chloro-phenyl)-[1-(2-morpholin-4-yl-ethyl)-1H-indol-3-ylmethyl]-amine | 1206536-25-5

• 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: (4-chloro-phenyl)-[1-(2-morpholin-4-yl-ethyl)-1H-indol-3-ylmethyl]-amine
• 英文别名: 4-chloro-N-({1-[2-(morpholin-4-yl)ethyl]-1H-indol-3-yl}methyl)aniline, 9；4-chloro-N-[[1-(2-morpholin-4-ylethyl)indol-3-yl]methyl]aniline
• CAS: 1206536-25-5
• 化学式: C₂₁H₂₄ClN₃O
• 分子量: 369.894
• InChiKey: TVUIXGOGLUNYIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 palladium on carbon 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 (4-chloro-phenyl)-[1-(2-morpholin-4-yl-ethyl)-1H-indol-3-ylmethyl]-amine
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Analogs of Indole-Based Cannabimimetic Agents

  摘要：

  Aminoalkylindoles (AAIs), although structurally dissimilar from the classical cannabinoids, are known to be capable of binding to cannabinoid receptors and of evoking cannabinomimetic responses. With the aim of investigating the structure–activity relationships (SAR) for the binding of non‐classical agonists to CB1 and CB2 cannabinoid receptors, we designed and synthesized a series of indole derivatives. The compounds were tested for their analgesic action by formalin test and compared to WIN 55212‐2, an AAI acting to the cannabinoid receptors. In receptor binding assay, compound 5 showed affinity for the CB1 receptor comparable to WIN 55212‐2.

  DOI：

  10.1111/j.1747-0285.2009.00910.x

文献信息

• Synthesis and Pharmacological Evaluation of Analogs of Indole-Based Cannabimimetic Agents
  作者：Orazio Mazzoni、Maria V. Diurno、Antonio M. di Bosco、Ettore Novellino、Paolo Grieco、Giovanni Esposito、Alessia Bertamino、Antonio Calignano、Roberto Russo

  DOI：10.1111/j.1747-0285.2009.00910.x

  日期：2010.1

  Aminoalkylindoles (AAIs), although structurally dissimilar from the classical cannabinoids, are known to be capable of binding to cannabinoid receptors and of evoking cannabinomimetic responses. With the aim of investigating the structure–activity relationships (SAR) for the binding of non‐classical agonists to CB1 and CB2 cannabinoid receptors, we designed and synthesized a series of indole derivatives. The compounds were tested for their analgesic action by formalin test and compared to WIN 55212‐2, an AAI acting to the cannabinoid receptors. In receptor binding assay, compound 5 showed affinity for the CB1 receptor comparable to WIN 55212‐2.