6-(2-N,N-dimethylaminoethyl)benzo[d]isothiazolo[2,3-a]indol-S,S-dioxide

• 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: 6-(2-N,N-dimethylaminoethyl)benzo[d]isothiazolo[2,3-a]indol-S,S-dioxide
• 英文别名: 2-(5,5-dioxoindolo[1,2-b][1,2]benzothiazol-11-yl)-N,N-dimethylethanamine
• 化学式: C₁₈H₁₈N₂O₂S
• 分子量: 326.419
• InChiKey: RMDVLYWQLPVFAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  N,N-二甲基色胺 在 四(三苯基膦)钯 、 18-冠醚-6 、 potassium tert-butylate 、 potassium acetate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-(2-N,N-dimethylaminoethyl)benzo[d]isothiazolo[2,3-a]indol-S,S-dioxide
  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

• [EN] TETRACYCLIC ARYLSULFONYL INDOLES HAVING SEROTONIN RECEPTOR AFFINITY<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 LIFE SCIENCES LTD

  公开号：WO2004000849A3

  公开（公告）日：2004-03-25
• 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.
• Interaction of N1-unsubstituted and N1-benzenesulfonyltryptamines at h5-HT6 receptors
  作者：Renata Kolanos、Małgorzata Dukat、Bryan L. Roth、Richard A. Glennon

  DOI：10.1016/j.bmcl.2006.08.068

  日期：2006.11

  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.