3-(1-乙基吡咯烷-3-基)-1H-吲哚 | 3671-01-0

• 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
• 中文名称: 3-(1-乙基吡咯烷-3-基)-1H-吲哚
• 英文名称: 3-(1-ethyl-pyrrolidin-3-yl)-indole
• 英文别名: (+/-)-1-Ethyl-3-(indol-3-yl)-pyrrolidin；3-(1-Ethylpyrrolidin-3-yl)-indol；3-(1-ethylpyrrolidin-3-yl)-1H-indole
• CAS: 3671-01-0
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: GINDSTSZDIENFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-(1-乙基吡咯烷-3-基)-1H-吲哚 在 四(三苯基膦)钯 、 potassium acetate 、 sodium hydride 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (R,S) 10-(1-ethylpyrrolidin-3-yl)-5-thia-4b-aza-indeno[2,1-a]indene 5,5-dioxide
  参考文献：
  名称：

  Synthesis and Structure Activity Relationship of Rigidized Indolyl Pyrrolidine Derivatives as 5-HT6 Receptor Ligands

  摘要：

  一系列新型刚性吲哚基吡咯烷衍生物通过限制色氨酸胺氮原子与a和b碳的结合而设计。所有合成的衍生物在体外结合测定中对5-HT6R表现出中等亲和力。本通讯的主题是选定化合物的合成、结构活性关系（SAR）、药代动力学特征以及体内疗效。

  DOI：

  10.14233/ajchem.2013.15443
• 作为产物：
  描述：

  N-乙基马来酰亚胺 在 lithium aluminium tetrahydride 、 magnesium 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 3-(1-乙基吡咯烷-3-基)-1H-吲哚
  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

• EP2724156B1
  申请人：——

  公开号：EP2724156B1

  公开（公告）日：2017-08-16
• 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.
• Synthesis and Structure Activity Relationship of Rigidized Indolyl Pyrrolidine Derivatives as 5-HT6 Receptor Ligands
  作者：Ramakrishna Nirogi、Adireddy Dwarampudi、Venugopalarao Bhatta、Laxman Kota、P.K. Dubey

  DOI：10.14233/ajchem.2013.15443

  日期：——

  A novel series of rigidized indolyl pyrrolidine derivatives have been designed by constraining the tryptamine nitrogen through a and b carbons. All the synthesized derivatives have shown moderate affinities at 5-HT6R when tested in in vitro binding assay. Synthesis, structure activity relationship (SAR), pharmacokinetic profile and in vivo efficacy of a selected compound is the subject matter of this communication.

  一系列新型刚性吲哚基吡咯烷衍生物通过限制色氨酸胺氮原子与a和b碳的结合而设计。所有合成的衍生物在体外结合测定中对5-HT6R表现出中等亲和力。本通讯的主题是选定化合物的合成、结构活性关系（SAR）、药代动力学特征以及体内疗效。