(2S)-(-)-3-[(2S,4R)-4-(4,5-dimethoxybenzo[b]thiophen-2-yl)-2-methylpiperidinyl]-1-(1H-indol-4-yl)oxy-2-propanol | 346589-10-4

• 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: (2S)-(-)-3-[(2S,4R)-4-(4,5-dimethoxybenzo[b]thiophen-2-yl)-2-methylpiperidinyl]-1-(1H-indol-4-yl)oxy-2-propanol
• 英文别名: (S)-1-[(4S,6R)-4-(4,5-Dimethoxy-benzo[b]thiophen-2-yl)-2-methyl-piperidin-1-yl]-3-(1H-indol-4-yloxy)-propan-2-ol；(2S)-1-[(2S,4R)-4-(4,5-dimethoxy-1-benzothiophen-2-yl)-2-methylpiperidin-1-yl]-3-(1H-indol-4-yloxy)propan-2-ol
• CAS: 346589-10-4
• 化学式: C₂₇H₃₂N₂O₄S
• 分子量: 480.628
• InChiKey: IYVOISDYTHXCOF-OTWHNJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  草酸 、 (2S)-(-)-3-[(2S,4R)-4-(4,5-dimethoxybenzo[b]thiophen-2-yl)-2-methylpiperidinyl]-1-(1H-indol-4-yl)oxy-2-propanol 以 乙酸乙酯 为溶剂， 以98%的产率得到(2S)-(-)-3-[(2S,4R)-4-(4,5-Dimethoxybenzo[b]thiophen-2-yl)-2-methylpiperidinyl]-1-(1H-indol-4-yl)oxy-2-propanol oxalate
  参考文献：
  名称：

  Indole derivatives for the treatment of depression and anxiety

  摘要：

  本发明提供了以下化合物的公式（I）：这些化合物对治疗抑郁症、焦虑症，并缓解因戒烟或部分戒烟引起的症状非常有用。

  公开号：

  US20040006229A1
• 作为产物：
  描述：

  4-(4,5-Dimethoxy-benzo[b]thiophen-2-yl)-4-hydroxy-2-methyl-piperidine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2S)-(-)-3-[(2S,4R)-4-(4,5-dimethoxybenzo[b]thiophen-2-yl)-2-methylpiperidinyl]-1-(1H-indol-4-yl)oxy-2-propanol
  参考文献：
  名称：

  Advances Toward new antidepressants beyond SSRIs: 1-aryloxy-3-piperidinylpropan-2-ols with dual 5-HT1A receptor antagonism/SSRI activities. Part 2

  摘要：

  Potent 5-HT1A/SSRIs at low nanomolar and subnanomolar concentrations were identified in a series of 1-(1H-indol-4-yloxy)-3-(4-benzo[b]thiophen-2-ylpiperidinyl)propan-2-ols. Incorporation of an alpha-Me group in the piperidine ring with its specific stereochemistry enhanced binding affinity at the 5-HT reuptake site and in vitro 5-HT1A antagonist functional activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00392-5

文献信息

• Indole derivatives for the treatment of depression and anxiety
  申请人：——

  公开号：US20040006229A1

  公开（公告）日：2004-01-08

  The present invention provides compounds of formula (I): which are useful for treating depression, anxiety, and alleviating the symptoms caused by withdrawal or partial withdrawal from the use of tobacco or of nicotine. 1

  本发明提供了以下化合物的公式（I）：这些化合物对治疗抑郁症、焦虑症，并缓解因戒烟或部分戒烟引起的症状非常有用。
• Advances Toward new antidepressants beyond SSRIs: 1-aryloxy-3-piperidinylpropan-2-ols with dual 5-HT1A receptor antagonism/SSRI activities. Part 2
  作者：Kumiko Takeuchi、Todd J Kohn、Nicholas A Honigschmidt、Vincent P Rocco、Patrick G Spinazze、Daniel J Koch、Steven T Atkinson、Larry W Hertel、David L Nelson、D.Bradley Wainscott、Laura J Ahmad、Janice Shaw、Penny G Threlkeld、David T Wong

  DOI：10.1016/s0960-894x(03)00392-5

  日期：2003.7

  Potent 5-HT1A/SSRIs at low nanomolar and subnanomolar concentrations were identified in a series of 1-(1H-indol-4-yloxy)-3-(4-benzo[b]thiophen-2-ylpiperidinyl)propan-2-ols. Incorporation of an alpha-Me group in the piperidine ring with its specific stereochemistry enhanced binding affinity at the 5-HT reuptake site and in vitro 5-HT1A antagonist functional activity. (C) 2003 Elsevier Science Ltd. All rights reserved.