trans-(2S)-(-)-3-(2-methyl-4-(3-methylbenzo[b]thiophen-5-yl)piperidin-1-yl)-1-(2-methylindol-4-yl)oxy-2-propanol | 346591-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: trans-(2S)-(-)-3-(2-methyl-4-(3-methylbenzo[b]thiophen-5-yl)piperidin-1-yl)-1-(2-methylindol-4-yl)oxy-2-propanol
• 英文别名: (2S)-1-[(2-methyl-1H-indol-4-yl)oxy]-3-[(2S,4R)-2-methyl-4-(3-methyl-1-benzothiophen-5-yl)piperidin-1-yl]propan-2-ol
• CAS: 346591-36-4
• 化学式: C₂₇H₃₂N₂O₂S
• 分子量: 448.629
• InChiKey: QNRJDGABFBSZCM-NNWRFLSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯磺酸 、 trans-(2S)-(-)-3-(2-methyl-4-(3-methylbenzo[b]thiophen-5-yl)piperidin-1-yl)-1-(2-methylindol-4-yl)oxy-2-propanol 以 乙酸乙酯 、 异丙醇 为溶剂， 以81.1%的产率得到trans-(2S)-(-)-3-(2-methyl-4-(3-methylbenzo[b]thiophen-5-yl)piperidin-1-yl)-1-(2-methylindol-4-yl)oxy-2-propanol benzenesulfonate
  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：

  3-甲基-5-溴苯并噻吩 在 silica gel 、 钯 、 polyethylenimine 1,1-二溴乙烷 、 氢气 、 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 甲苯 为溶剂， 生成 trans-(2S)-(-)-3-(2-methyl-4-(3-methylbenzo[b]thiophen-5-yl)piperidin-1-yl)-1-(2-methylindol-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 4

  摘要：

  A series of 1-(1H-indol-4-yloxy)-3-(4-arylpiperidinyl)propan-2-ols possessing potent dual 5-HT1A receptor antagonism and serotonin reuptake inhibition was discovered. The fused aryl ring moiety contributed to the robust dual activities irrespective of the regiochemistry associated with its connectivity to the piperidine central ring. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.088

文献信息

• INDOLE DERIVATIVES FOR THE TREATMENT OF DEPRESSION AND ANXIETY
  申请人：ELI LILLY AND COMPANY

  公开号：EP1242411B1

  公开（公告）日：2006-03-08
• US7144898B2
  申请人：——

  公开号：US7144898B2

  公开（公告）日：2006-12-05
• [EN] METHODS OF USING COMPOUNDS WITH COMBINED 5-HT1A AND SSRI ACTIVITIES AS-NEEDED TO TREAT SEXUAL DYSFUNCTION<br/>[FR] METHODES D'UTILISATION DE COMPOSES PRESENTANT DES ACTIVITES COMBINEES 5-HT1A ET SSRI, EN FONCTION DES BESOINS, POUR TRAITER DYSFONCTION SEXUELLE
  申请人：DYNOGEN PHARMACEUTICALS INC

  公开号：WO2004082686A2

  公开（公告）日：2004-09-30

  A method is provided for using compounds that exhibit combined activities as 5-HT1A active agents and selective serotonin reuptake inhibitors (SSRI’s) to treat sexual dysfunction, particularly premature ejaculation, on an as-needed basis shortly before sexual activity.
• 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 4
  作者：Vincent P. Rocco、Patrick G. Spinazze、Todd J. Kohn、Nicholas A. Honigschmidt、David L. Nelson、D. Bradley Wainscott、Laura J. Ahmad、Janice Shaw、Penny G. Threlkeld、David T. Wong、Kumiko Takeuchi

  DOI：10.1016/j.bmcl.2004.02.088

  日期：2004.5

  A series of 1-(1H-indol-4-yloxy)-3-(4-arylpiperidinyl)propan-2-ols possessing potent dual 5-HT1A receptor antagonism and serotonin reuptake inhibition was discovered. The fused aryl ring moiety contributed to the robust dual activities irrespective of the regiochemistry associated with its connectivity to the piperidine central ring. (C) 2004 Elsevier Ltd. All rights reserved.