3-{8-[3-(1H-indol-4-yloxy)propyl]-8-azabicyclo[3.2.1]oct-2-en-3-yl}-1H-indole

• 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: 3-{8-[3-(1H-indol-4-yloxy)propyl]-8-azabicyclo[3.2.1]oct-2-en-3-yl}-1H-indole
• 英文别名: 1H-4-indolyl 3-[3-(1H-3-indolyl)-8-azabicyclo[3.2.1]oct-2-en-8-yl]propyl ether；3-[8-[3-(1H-indol-4-yloxy)propyl]-8-azabicyclo[3.2.1]oct-2-en-3-yl]-1H-indole
• 化学式: C₂₆H₂₇N₃O
• 分子量: 397.52
• InChiKey: RDPZHUVLZFXTFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  托品酮 在 sodium hydroxide 、 1-氯乙基氯甲酸酯 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 异丙醇 、 乙腈 为溶剂， 生成 3-{8-[3-(1H-indol-4-yloxy)propyl]-8-azabicyclo[3.2.1]oct-2-en-3-yl}-1H-indole
  参考文献：
  名称：

  Novel aryloxy-8-azabicyclo[3.2.1]oct-3-enes with 5-HT transporter and 5-HT1A affinity

  摘要：

  Joining aryl 8-azabicyclo[3.2.1]oct-3-enes with aryloxyethanes and aryloxypropanes produces novel series of compounds 11 and 12 with potent 5-HT-T affinity and moderately potent 5-HT1A affinity. Moreover, several of these compounds possess functional 5-HT1A antagonism. Optimal compounds are, 4-indolyloxyethane 21, 4-indolyloxypropanes 25, and 27, which possess potent 5-HT-T affinity (5-HT-T K-i: 21: 1.2 nM, 25: 0.54 nM, 27: 0.38 nM) and good 5-HT1A affinity/antagonism (5-HT1A K-i, [S-35]GTPgammaS: E-max (%): 21: 111.1 nM, 0% 25: 173.2 nM, 0%; 27: 107 nM, 0%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.030

文献信息

• Aryl-8-azabicyclo [3.2.1] octanes for the treatment of depression
  申请人：Wyeth

  公开号：US20030032645A1

  公开（公告）日：2003-02-13

  The present invention includes compounds of formula I 1 wherein A, X, n, Ar 1 , and Ar 2 are defined as set forth herein. These compounds may be used to treat depression. The invention also includes formulations containing these compounds, and methods for making and using compounds of this invention.

  本发明包括式I1的化合物，其中A、X、n、Ar1和Ar2如本文所述。这些化合物可用于治疗抑郁症。本发明还包括含有这些化合物的配方，以及制备和使用本发明化合物的方法。
• ARYL-8-AZABICYCLO 3.2.1]OCTANES FOR THE TREATMENT OF DEPRESSION
  申请人：Wyeth

  公开号：EP1390364B1

  公开（公告）日：2004-09-29
• US6632824B2
  申请人：——

  公开号：US6632824B2

  公开（公告）日：2003-10-14
• Novel aryloxy-8-azabicyclo[3.2.1]oct-3-enes with 5-HT transporter and 5-HT1A affinity
  作者：Adam M. Gilbert、Thomas Coleman、Jason Kodah、Richard E. Mewshaw、Rosemary Scerni、Lee E. Schechter、Deborah L. Smith、Terrance H. Andree

  DOI：10.1016/j.bmcl.2004.08.030

  日期：2004.11

  Joining aryl 8-azabicyclo[3.2.1]oct-3-enes with aryloxyethanes and aryloxypropanes produces novel series of compounds 11 and 12 with potent 5-HT-T affinity and moderately potent 5-HT1A affinity. Moreover, several of these compounds possess functional 5-HT1A antagonism. Optimal compounds are, 4-indolyloxyethane 21, 4-indolyloxypropanes 25, and 27, which possess potent 5-HT-T affinity (5-HT-T K-i: 21: 1.2 nM, 25: 0.54 nM, 27: 0.38 nM) and good 5-HT1A affinity/antagonism (5-HT1A K-i, [S-35]GTPgammaS: E-max (%): 21: 111.1 nM, 0% 25: 173.2 nM, 0%; 27: 107 nM, 0%). (C) 2004 Elsevier Ltd. All rights reserved.