2,4-difluoro-11-(2-N,N-dimethylaminoethyl)-6H-isoindolo[2,1-a]indole | 639808-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2,4-difluoro-11-(2-N,N-dimethylaminoethyl)-6H-isoindolo[2,1-a]indole
• 英文别名: 2-(2,4-difluoro-6H-isoindolo[2,1-a]indol-11-yl)-N,N-dimethylethanamine
• CAS: 639808-78-9
• 化学式: C₁₉H₁₈F₂N₂
• 分子量: 312.362
• InChiKey: GWRLSYAJDSMTNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 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：
  8.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-[1-(2-bromobenzyl)-5,7-difluoroindol-3-yl]ethyl-N,N-dimethylamine 在 四(三苯基膦)钯 、 potassium acetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 5.0h， 生成 2,4-difluoro-11-(2-N,N-dimethylaminoethyl)-6H-isoindolo[2,1-a]indole
  参考文献：
  名称：

  Synthesis and structure–activity relationship of novel conformationally restricted analogues of serotonin as 5-HT₆ receptor ligands

  摘要：

  5-Hydroxytryptamine 6 receptors (5-HT6R) are being perceived as the possible target for treatment of cognitive disorders as well as obesity. The present article deals with the design, synthesis, in vitro binding and structure-activity relationship of a novel series of tetracyclic tryptamines with the rigidized N-arylsulphonyl, N-arylcarbonyl and N-benzyl substituents as 5-HT6 receptor ligands. The chiral sulphonyl derivatives 15a and 17a showed high affinity at 5-HT6R with the K-i of 23.4 and 20.5 nM, respectively. The lead compound from the series 15a has acceptable ADME properties, adequate brain penetration and is active in animal models of cognition like Novel Object Recognition Task (NORT) and water maze.

  DOI：

  10.3109/14756366.2011.595713

文献信息

• [EN] ARYLALKYL INDOLES HAVING SERTONIN RECEPTOR AFFINITY USEFUL AS THERAPEUTIC AGENTS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] ARYLALKYL INDOLES A AFFINITE DE RECEPTEUR DE LA SEROTONINE UTILISES COMME AGENTS THERAPEUTIQUES, LEUR PROCEDE DE PREPARATION ET COMPOSITIONS PHARMACEUTIQUES CONTENANT LESDITS INDOLES
  申请人：SUVEN PHARMACEUTICALS LTD

  公开号：WO2004000845A1

  公开（公告）日：2003-12-31

  The present invention relates to novel tetracyclic arylalkyl indoles, their derivatives, their analogues, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates, novel intermediates described herein and pharmaceutically acceptable compositions containing them. This invention particularly relates to novel tetracyclic arylalkyl of the general formula (I), their derivatives, their analogues, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates, novel intermediates described herein and pharmaceutically acceptable compositions containing them. This invention also relates to process/es for preparing such compound/s of general formula (I), composition/s containing effective amount/s of such a compound and the use of such a compound/composition in therapy.

  本发明涉及新型四环芳基烷基吲哚化合物，其衍生物，类似物，互变异构体，立体异构体，多晶形态，药用可接受的盐，药用可接受的溶剂化合物，本文描述的新中间体以及含有它们的药用可接受的组合物。本发明特别涉及一般式（I）的新型四环芳基烷基化合物，其衍生物，类似物，互变异构体，立体异构体，多晶形态，药用可接受的盐，药用可接受的溶剂化合物，本文描述的新中间体以及含有它们的药用可接受的组合物。本发明还涉及制备一般式（I）化合物的方法/方法，含有这种化合物的有效量/量的组合物以及这种化合物/组合物在治疗中的使用。
• Arylalkyl indoles having serotonin receptor affinity useful as therapeutic agents, process for their preparation and pharmaceutical compositions containing them
  申请人：Jasti Venkateswarlu

  公开号：US20050203103A1

  公开（公告）日：2005-09-15

  The present invention relates to novel tetracyclic arylalkyl indoles, their derivatives, their analogues, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates, novel intermediates described herein and pharmaceutically acceptable compositions containing them. This invention particularly relates to novel tetracyclic arylalkyl of the general formula (I), their derivatives, their analogues, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates, novel intermediates described herein and pharmaceutically acceptable compositions containing them. This invention also relates to process/es for preparing such compound/s of general formula (I), composition/s containing effective amount/s of such a compound and the use of such a compound/composition in therapy.

  本发明涉及新型四环芳烷基吲哚、它们的衍生物、它们的类似物、它们的同分异构体、它们的立体异构体、它们的多晶型、它们的药学上可接受的盐、它们的药学上可接受的溶解物、本文所述的新型中间体以及含有它们的药学上可接受的组合物。本发明尤其涉及通式（I）的新型四环芳烷基、其衍生物、其类似物、其同分异构体、其立体异构体、其多晶型、其药学上可接受的盐、其药学上可接受的溶解物、本文所述的新型中间体以及含有它们的药学上可接受的组合物。本发明还涉及制备通式（I）化合物的工艺、含有有效量此类化合物的组合物以及此类化合物/组合物在治疗中的用途。
• ARYLALKYL INDOLES HAVING SEROTONIN RECEPTOR AFFINITY USEFUL AS THERAPEUTIC AGENTS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Suven Pharmaceuticals Ltd.

  公开号：EP1537113A1

  公开（公告）日：2005-06-08
• US7297711B2
  申请人：——

  公开号：US7297711B2

  公开（公告）日：2007-11-20