3-(2-Amino-ethyl)-6,7-benzindol | 54544-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(2-Amino-ethyl)-6,7-benzindol
• 英文别名: 2-(1H-benzo[g]indol-3-yl)ethanamine；2-(1H-benzo[g]indol-3-yl)ethylamine
• CAS: 54544-35-3
• 化学式: C₁₄H₁₄N₂
• 分子量: 210.279
• InChiKey: QNNMQBJKVGKLGI-UHFFFAOYSA-N

物化性质

• 沸点：
  443.7±20.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 3-(2-Amino-ethyl)-6,7-benzindol 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-(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
• 作为产物：
  描述：

  在 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以8.6 mg的产率得到3-(2-Amino-ethyl)-6,7-benzindol
  参考文献：
  名称：

  一种合成色胺和其他杂环的权宜之计。

  摘要：

  DOI：

  10.1002/anie.200800404

文献信息

• An Expedient Strategy for the Synthesis of Tryptamines and Other Heterocycles
  作者：K. C. Nicolaou、Arkady Krasovskiy、Vincent É. Trépanier、David Y.-K. Chen

  DOI：10.1002/anie.200800404

  日期：2008.5.19
• Nicolaou, K. C.; Krasovskiy, Arkady; Majumder, Utpal, Journal of the American Chemical Society, 2009, vol. 131, p. 3690 - 3699
  作者：Nicolaou, K. C.、Krasovskiy, Arkady、Majumder, Utpal、Trepanier, Vincent E.、Chen, David Y.-K.

  DOI：——

  日期：——
• Synthesis and structure–activity relationship of novel conformationally restricted analogues of serotonin as 5-HT₆ receptor ligands
  作者：Ramakrishna V.S. Nirogi、Ramasastri Kambhampati、Prabhakar Kothmirkar、Jagadishbabu Konda、Thrinath Reddy Bandyala、Parandhama Gudla、Sobhanadri Arepalli、Narasimhareddy P. Gangadasari、Anil K. Shinde、Amol D. Deshpande、Adireddy Dwarampudi、Anil K. Chindhe、Pramod Kumar Dubey

  DOI：10.3109/14756366.2011.595713

  日期：2012.6.1

  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.