6-chloro-1-(2-bromobenzenesulfonyl)-3-(4-methylpiperazin-1-yl)-1H-indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-chloro-1-(2-bromobenzenesulfonyl)-3-(4-methylpiperazin-1-yl)-1H-indole
• 英文别名: 1-(2-bromophenyl)sulfonyl-6-chloro-3-(4-methylpiperazin-1-yl)indole
• 化学式: C₁₉H₁₉BrClN₃O₂S
• 分子量: 468.802
• InChiKey: FQELGEQWCXYSFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 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：
  53.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-chloro-3-(4-methylpiperazin-1-yl)-1H-indole 、 2-溴苯磺酰氯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.75h， 生成 6-chloro-1-(2-bromobenzenesulfonyl)-3-(4-methylpiperazin-1-yl)-1H-indole
  参考文献：
  名称：

  Indole-3-piperazinyl derivatives: Novel chemical class of 5-HT6 receptor antagonists

  摘要：

  N-1-Arylsulfonyl-3-piperazinyl indole derivatives were designed and identified as a novel class of 5-HT6 receptors ligands. All the compounds have high affinity and antagonist activity towards 5-HT6 receptor. The compound 7a (K-i = 3.4 nM, functional assay IC50 = 310 nM) shows enhanced cognitive effect when tested in NORT and Morris water maze models. Synthesis, SAR and PK profile of these novel compounds constitute the subject matter of this Letter. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.11.001

文献信息

• [EN] 3-(HETEROCYCLYL)-N-(ARYLSULFONYL)INDOLE DERIVATIVES AS FUNCTIONAL 5-HT6 LIGANDS<br/>[FR] DÉRIVÉS DU 3-(HÉTÉROCYCLYL)-N-(ARYLSULFONYL)INDOLE EN TANT QUE LIGANDS FONCTIONNELS DE LA 5-HT6
  申请人：SUVEN LIFE SCIENCES LTD

  公开号：WO2007138611A1

  公开（公告）日：2007-12-06

  [EN] The present invention provides 3-(Heterocyclyl)-N-(arylsulfonyl)indole derivatives of formula (I), which are useful in treatment of CNS disorders that are related to 5-HTg receptor function. The compounds of this invention bind selectively with high affinity to 5-HTg receptor. The present invention also discloses the methods of preparation of these ligands and medicine containing the said compound/s.
  [FR] La présente invention concerne des dérivés du 3-(hétérocyclyl)-N-(arylsulfonyl)indole de formule (I), utilisables pour traiter les affections du SNC liées à la fonction du récepteur de la 5-HTg. Les composés de la présente invention se lient sélectivement avec une affinité élevée au récepteur de la 5-HTg. L'invention concerne également les procédés de préparation de ces ligands et un médicament contenant ledit ou lesdits composés.
• Indole-3-piperazinyl derivatives: Novel chemical class of 5-HT6 receptor antagonists
  作者：Ramakrishna V.S. Nirogi、Amol D. Deshpande、Ramasastri Kambhampati、Rajesh Kumar Badange、Laxman Kota、Anand V. Daulatabad、Anil K. Shinde、Ishtiyaque Ahmad、Vishwottam Kandikere、Pradeep Jayarajan、P.K. Dubey

  DOI：10.1016/j.bmcl.2010.11.001

  日期：2011.1

  N-1-Arylsulfonyl-3-piperazinyl indole derivatives were designed and identified as a novel class of 5-HT6 receptors ligands. All the compounds have high affinity and antagonist activity towards 5-HT6 receptor. The compound 7a (K-i = 3.4 nM, functional assay IC50 = 310 nM) shows enhanced cognitive effect when tested in NORT and Morris water maze models. Synthesis, SAR and PK profile of these novel compounds constitute the subject matter of this Letter. (C) 2010 Published by Elsevier Ltd.