1-(5-甲氧基-1H-吲哚-3-基)-N,N-二甲基丙烷-2-胺 | 101831-90-7

• 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
• 中文名称: 1-(5-甲氧基-1H-吲哚-3-基)-N,N-二甲基丙烷-2-胺
• 英文名称: N,N-Dimethyl-5-methoxy-alpha-methyltryptamine
• 英文别名: 1-(5-methoxy-1H-indol-3-yl)-N,N-dimethylpropan-2-amine
• CAS: 101831-90-7
• 化学式: C₁₄H₂₀N₂O
• 分子量: 232.326
• InChiKey: WDKDEBAFCKHQPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  28.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-甲氧基-1H-吲哚-3-基)-N,N-二甲基丙烷-2-胺 、 2-溴苯磺酰氯 在 四(三苯基膦)钯 、 potassium acetate 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-methoxy-11-[(2-N,N-dimethylamino-2-methyl)ethyl]benzo[d]isothiazolo[3,2-a]indol-S,S-dioxide
  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：

  聚合甲醛 、 Β-吲哚基乙胺 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 1-(5-甲氧基-1H-吲哚-3-基)-N,N-二甲基丙烷-2-胺
  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

文献信息

• 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.