3-(1-benzylpyrrolidin-3-yl)-1-(2-bromophenylsulfonyl)-1H-indole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(1-benzylpyrrolidin-3-yl)-1-(2-bromophenylsulfonyl)-1H-indole
• 英文别名: 3-(1-Benzyl-pyrrolidin-3-yl)-1-(2-bromo-benzenesulfonyl)-1H-indole；3-(1-benzylpyrrolidin-3-yl)-1-(2-bromophenyl)sulfonylindole
• 化学式: C₂₅H₂₃BrN₂O₂S
• 分子量: 495.44
• InChiKey: AZXATNGYDIGGJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-benzyl-3-(1H-indole-3-yl)pyrrolidine-2,5-dione 在 lithium aluminium tetrahydride 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 3-(1-benzylpyrrolidin-3-yl)-1-(2-bromophenylsulfonyl)-1H-indole
  参考文献：
  名称：

  Conformationally constrained N1-arylsulfonyltryptamine derivatives as 5-HT6 receptor antagonists

  摘要：

  Several series of conformationally constrained N-1-arylsulfonyltryptamine derivatives were prepared and tested for 5-HT6 receptor binding affinity and ability to modulate cAMP production in a cyclase assay. The 3-piperidin-3-yl-, 3-(1-methylpyrrolidin-2-ylmethyl)-, and 3-pyrrolidin-3-yl-1H-indole arrays (8-13) appear to be able to adopt a conformation that allows high affinity 5-HT6 receptor binding, while the beta-carboline array 14 binds with a significantly weaker (10- to 100-fold) affinity. N-1-Benzenesulfonyl-3-piperidin-3-yl-1H-indole 9a is a high affinity full agonist with EC50 = 24 nM. Several of the N-1-arylsulfonyl-3-(1-methylpyrrolidin-2-ylmethyl)-1H-indole derivatives behave as very potent antagonists ((S)- 11r, (S)- 11t; IC50 = 0.8, 1.0 nM). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.028

文献信息

• Heterocyclylindazole and -azaindazole compounds as 5-hydroxytryptamine-6 ligands
  申请人：American Home Products Corporation

  公开号：US20020198213A1

  公开（公告）日：2002-12-26

  The present invention provides a compound of formula I and the use thereof in the therapeutic treatment of disorders related to or affected by the 5-HT6 receptor. 1

  本发明提供了I式化合物及其在治疗与5-HT6受体相关或受其影响的疾病中的应用。
• Heterocyclindazole and -azaindazole compounds as 5-hydroxytryptamine-6 ligands
  申请人：Wyeth

  公开号：EP1803720A1

  公开（公告）日：2007-07-04

  The present invention provides a compound of formula I and the use thereof in the therapeutic treatment of disorders related to or affected by the 5-HT6 receptor.

  本发明提供了一种式 I 化合物及其在治疗与 5-HT6 受体有关或受其影响的疾病中的用途。
• HETEROCYCLINDAZOLE AND AZAINDAZOLE COMPOUNDS AS 5-HYDROXYTRYPTAMINE-6 LIGANDS
  申请人：Wyeth

  公开号：EP1355904B1

  公开（公告）日：2007-08-01
• US6767912B2
  申请人：——

  公开号：US6767912B2

  公开（公告）日：2004-07-27
• US6903112B2
  申请人：——

  公开号：US6903112B2

  公开（公告）日：2005-06-07