2-(1-(2-bromobenzyl)-1H-benzo[g]indol-3-yl)-N,N-dimethylethan-1-amine | 1375501-73-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-(2-bromobenzyl)-1H-benzo[g]indol-3-yl)-N,N-dimethylethan-1-amine
• CAS: 1375501-73-7
• 化学式: C₂₃H₂₃BrN₂
• 分子量: 407.353
• InChiKey: OUIABXZPPQIJQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  8.17
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(1-(2-bromobenzyl)-1H-benzo[g]indol-3-yl)-N,N-dimethylethan-1-amine 在 四(三苯基膦)钯 、 potassium acetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 5.0h， 生成 2-(12H-benzo[g]isoindolo[2,1-a]indol-7-yl)-N,N-dimethylethan-1-amine
  参考文献：
  名称：

  Synthesis and structure–activity relationship of novel conformationally restricted analogues of serotonin as 5-HT₆ receptor ligands

  摘要：

  5-Hydroxytryptamine 6 receptors (5-HT6R) are being perceived as the possible target for treatment of cognitive disorders as well as obesity. The present article deals with the design, synthesis, in vitro binding and structure-activity relationship of a novel series of tetracyclic tryptamines with the rigidized N-arylsulphonyl, N-arylcarbonyl and N-benzyl substituents as 5-HT6 receptor ligands. The chiral sulphonyl derivatives 15a and 17a showed high affinity at 5-HT6R with the K-i of 23.4 and 20.5 nM, respectively. The lead compound from the series 15a has acceptable ADME properties, adequate brain penetration and is active in animal models of cognition like Novel Object Recognition Task (NORT) and water maze.

  DOI：

  10.3109/14756366.2011.595713
• 作为产物：
  描述：

  2-(1H-benzo[g]indol-3-yl)-N,N-dimethylethan-1-amine 、 2-溴苄氯 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(1-(2-bromobenzyl)-1H-benzo[g]indol-3-yl)-N,N-dimethylethan-1-amine
  参考文献：
  名称：

  Synthesis and structure–activity relationship of novel conformationally restricted analogues of serotonin as 5-HT₆ receptor ligands

  摘要：

  5-Hydroxytryptamine 6 receptors (5-HT6R) are being perceived as the possible target for treatment of cognitive disorders as well as obesity. The present article deals with the design, synthesis, in vitro binding and structure-activity relationship of a novel series of tetracyclic tryptamines with the rigidized N-arylsulphonyl, N-arylcarbonyl and N-benzyl substituents as 5-HT6 receptor ligands. The chiral sulphonyl derivatives 15a and 17a showed high affinity at 5-HT6R with the K-i of 23.4 and 20.5 nM, respectively. The lead compound from the series 15a has acceptable ADME properties, adequate brain penetration and is active in animal models of cognition like Novel Object Recognition Task (NORT) and water maze.

  DOI：

  10.3109/14756366.2011.595713