1-(benzenesulfonyl)-3-(1-methylpyrrolidin-3-yl)-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: 1-(benzenesulfonyl)-3-(1-methylpyrrolidin-3-yl)-1H-indole
• 英文别名: (R,S)-1-benzenesulfonyl-3-(1-methylpyrrolidin-3-yl)-1H-indole；1-(Benzenesulfonyl)-3-(1-methylpyrrolidin-3-yl)indole
• 化学式: C₁₉H₂₀N₂O₂S
• 分子量: 340.446
• InChiKey: UEMBANHXOBGHAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  50.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(benzenesulfonyl)-3-(1-methylpyrrolidin-3-yl)-1H-indole 在 二氯双(三邻甲苯膦)合钯(II) potassium acetate 作用下， 以 异丁酰胺 为溶剂， 反应 16.0h， 生成 10-(1-methylpyrrolidin-3-yl)-5-thia-4b-aza-indeno-[2,1-a]indene-5,5-dioxide
  参考文献：
  名称：

  WO2005/66184

  摘要：

  公开号：
• 作为产物：
  描述：

  吲哚 在 lithium aluminium tetrahydride 、 sodium hydride 、 magnesium 、 碘甲烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 1-(benzenesulfonyl)-3-(1-methylpyrrolidin-3-yl)-1H-indole
  参考文献：
  名称：

  Rigidized 1-aryl sulfonyl tryptamines: Synthesis and pharmacological evaluation as 5-HT6 receptor ligands

  摘要：

  A series of N-1-arylsulfonyl-3-(pyrrolidin-3-yl)-1H-indole and N-1-arylsulfonyl-3-(4-chloro-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole derivatives (tryptamine derivatives with rigidized side chain) have been prepared and tested for their binding affinity to 5-HT6 receptor. Several compounds displayed potent binding affinity for the 5-HT6 receptor when tested in in vitro binding assay. The primary SAR indicates that rigidification of dimethylamino alkyl chain at C-3 of indole carbon maintains the binding affinity to 5-HT6R. The lead compound N-1-benzenesulfonyl-3-(4-chloro-1-methyl-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole, 10a (K-b = 0.1 nM) has shown excellent in vitro affinity and was active in animal models of cognition like NORT and water maze. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.106

文献信息

• [EN] 3-(PYROLIDIN-3-L) INDOLES AS 5-HT6 RECEPTOR MODULATORS<br/>[FR] 3-(PYRROLIDINE-3-L)INDOLES EN TANT QUE MODULATEURS DU RECEPTEUR 5-HT6
  申请人：SUVEN LIFE SCIENCES

  公开号：WO2005066157A1

  公开（公告）日：2005-07-21

  The present invention describes 3-(Heterocyclic)indoles with the Formula (I), its stereoisomers and salts, wherein the substituents such as R, R1, R2, R3, R4, R10, R11, R12, R13, and R14 are described in the specification. The invention also provides a method to prepare compound with formula (I), pharmaceutical composition containing such compounds and method to manufacture a medicament. These compounds are useful in the treatment of various CNS disorders, hematological disorders, eating disorders, diseases associated with pain, respiratory disease, genito-urological disorders, cardio vascular diseases and cancer.

  本发明描述了具有化学式(I)的3-(杂环)吲哚，其立体异构体和盐，其中取代基如R、R1、R2、R3、R4、R10、R11、R12、R13和R14在说明书中有所描述。该发明还提供了制备具有化学式(I)的化合物的方法，含有这些化合物的药物组合物以及制造药物的方法。这些化合物在治疗各种中枢神经系统疾病、血液学疾病、进食障碍、与疼痛相关的疾病、呼吸系统疾病、泌尿生殖系统疾病、心血管疾病和癌症方面具有用途。
• NOVEL INDENO [2,1A]INDENES AND ISOINDOL [2,1-A]INDOLES
  申请人：Suven Life Sciences Limited

  公开号：EP1704154B1

  公开（公告）日：2009-05-06
• Novel indeno[2,1A]indenes and isoindolo[2,1-A]indoles
  申请人：Venkateswarlu Jasti

  公开号：US20070054946A1

  公开（公告）日：2007-03-08

  The present invention provides indeno[2,1a]indene and isoindolo[2,1-a]indole derivatives of the Formula I, its salts and its stereoisomers, wherein X, R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , R 13 and R 14 are as described in the specification. The invention also provides a method to prepare the compound of formula I, pharmaceutical composition containing such compounds, and method to manufacture a medicament. These compounds are useful in the treatment of various CNS disorders, hematological disorders, eating disorders, diseases associated with pain, respiratory diseases, genito-urological disorders, cardio vascular diseases and cancer.
• US7388024B2
  申请人：——

  公开号：US7388024B2

  公开（公告）日：2008-06-17
• Rigidized 1-aryl sulfonyl tryptamines: Synthesis and pharmacological evaluation as 5-HT6 receptor ligands
  作者：Ramakrishna Nirogi、Adireddy Dwarampudi、Ramasastry Kambhampati、Venugopalarao Bhatta、Laxman Kota、Anil Shinde、Rajesh Badange、Pradeep Jayarajan、Gopinadh Bhyrapuneni、P.K. Dubey

  DOI：10.1016/j.bmcl.2011.05.106

  日期：2011.8

  A series of N-1-arylsulfonyl-3-(pyrrolidin-3-yl)-1H-indole and N-1-arylsulfonyl-3-(4-chloro-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole derivatives (tryptamine derivatives with rigidized side chain) have been prepared and tested for their binding affinity to 5-HT6 receptor. Several compounds displayed potent binding affinity for the 5-HT6 receptor when tested in in vitro binding assay. The primary SAR indicates that rigidification of dimethylamino alkyl chain at C-3 of indole carbon maintains the binding affinity to 5-HT6R. The lead compound N-1-benzenesulfonyl-3-(4-chloro-1-methyl-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole, 10a (K-b = 0.1 nM) has shown excellent in vitro affinity and was active in animal models of cognition like NORT and water maze. (C) 2011 Elsevier Ltd. All rights reserved.