1-(2-bromophenylsulphonyl)-N,N-dimethyltryptamine | 639795-10-1

• 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: 1-(2-bromophenylsulphonyl)-N,N-dimethyltryptamine
• 英文别名: 2-[1-(2-bromophenylsulfonyl)indol-3-yl]ethyl-N,N-dimethylamine；2-[1-(2-bromophenyl)sulfonylindol-3-yl]-N,N-dimethylethanamine
• CAS: 639795-10-1
• 化学式: C₁₈H₁₉BrN₂O₂S
• 分子量: 407.331
• InChiKey: FFDWSXAXAUGQNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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-(2-bromophenylsulphonyl)-N,N-dimethyltryptamine 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 6-(2-N,N-dimethylaminoethyl)benzo[d]isothiazolo[2,3-a]indol-S,S-dioxide
  参考文献：
  名称：

  [EN] TETRACYCLIC ARYLSULFONYL INDOLES HAVING SEROTONIN RECEPTOR AFFINITY
  [FR] NOUVEAUX INDOLES TETRACYCLIQUES ARYLSULFONYLE AYANT UNE AFFINITE DU RECEPTEUR DE LA SEROTONINE ET UTILES COMME AGENTS THERAPEUTIQUES, LEUR PROCEDE DE PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT

  摘要：

  公开号：

  WO2004000849A3
• 作为产物：
  描述：

  N,N-二甲基色胺 、 2-溴苯磺酰氯 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 1-(2-bromophenylsulphonyl)-N,N-dimethyltryptamine
  参考文献：
  名称：

  Interaction of N1-unsubstituted and N1-benzenesulfonyltryptamines at h5-HT6 receptors

  摘要：

  Despite possessing a common tryptaminergic scaffold, examination of 28 (i.e., 14 pairs of) compounds suggests that N-1-unsubstituted and N-1-benzenesulfonyltryptamines likely bind at h5-HT6 receptors in a dissimilar manner (r(2) = 0.201). Additionally, an examination of two rotationally constrained N-1-benzenesulfonyltryptamine analogs indicates that a non-coplanar relationship between the two aryl groups might be preferred for interaction with the receptors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.068

文献信息

• Novel tetracyclic arylsulfonyl 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：US20050203154A1

  公开（公告）日：2005-09-15

  The present invention relates to novel tetracyclic arylsulfonyl 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 arylsulfonyl indoles 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磺酰基吲哚、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）的新型四环芳基磺酰基吲哚、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。
• Synthesis and structure–activity relationship of novel conformationally restricted analogues of serotonin as 5-HT₆ receptor ligands
  作者：Ramakrishna V.S. Nirogi、Ramasastri Kambhampati、Prabhakar Kothmirkar、Jagadishbabu Konda、Thrinath Reddy Bandyala、Parandhama Gudla、Sobhanadri Arepalli、Narasimhareddy P. Gangadasari、Anil K. Shinde、Amol D. Deshpande、Adireddy Dwarampudi、Anil K. Chindhe、Pramod Kumar Dubey

  DOI：10.3109/14756366.2011.595713

  日期：2012.6.1

  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.
• TETRACYCLIC ARYLSULFONYL INDOLES HAVING SEROTONIN RECEPTOR AFFINITY
  申请人：Suven Life Sciences Limited

  公开号：EP1523486A2

  公开（公告）日：2005-04-20
• US7649097B2
  申请人：——

  公开号：US7649097B2

  公开（公告）日：2010-01-19
• [EN] NOVEL TETRACYCLIC ARYLSULFONYL INDOLES HAVING SEROTONIN RECEPTOR AFFINITY USEFUL AS THERAPEUTIC AGENTS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX INDOLES TETRACYCLIQUES ARYLSULFONYLE AYANT UNE AFFINITE DU RECEPTEUR DE LA SEROTONINE ET UTILES COMME AGENTS THERAPEUTIQUES, LEUR PROCEDE DE PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SUVEN PHARMACEUTICALS LTD

  公开号：WO2004000849A2

  公开（公告）日：2003-12-31

  The present invention relates to novel tetracyclic arylsulfonyl indoles according to 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 particularly relates to novel tetracyclic arylsulfonyl indoles 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.