2-[3-(phenylsulfonyl)-1H-indol-4-yl]ethyl 4-methylbenzenesulfonate | 945000-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[3-(phenylsulfonyl)-1H-indol-4-yl]ethyl 4-methylbenzenesulfonate
• 英文别名: 2-[3-(benzenesulfonyl)-1H-indol-4-yl]ethyl 4-methylbenzenesulfonate
• CAS: 945000-91-9
• 化学式: C₂₃H₂₁NO₅S₂
• 分子量: 455.555
• InChiKey: PQUGTDYOMNHCFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[3-(phenylsulfonyl)-1H-indol-4-yl]ethyl 4-methylbenzenesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以93%的产率得到4-(2-azidoethyl)-3-(phenylsulfonyl)-1H-indole
  参考文献：
  名称：

  Dual acting norepinephrine reuptake inhibitors and 5-HT2A receptor antagonists: Identification, synthesis and activity of novel 4-aminoethyl-3-(phenylsulfonyl)-1H-indoles

  摘要：

  The discovery of a series of 4-aminoethyl-3-(phenylsulfonyl)-1H-indoles, dual acting norepinephrine reuptake inhibitors (NRIs) and 5-HT2A receptor antagonists, is described. The synthesis and structure-activity relationship (SAR) of this novel series of compounds is also presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.023
• 作为产物：
  描述：

  2-[3-(phenylsulfonyl)-1H-indol-4-yl]ethanol 、 对甲苯磺酰氯 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以91%的产率得到2-[3-(phenylsulfonyl)-1H-indol-4-yl]ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Dual acting norepinephrine reuptake inhibitors and 5-HT2A receptor antagonists: Identification, synthesis and activity of novel 4-aminoethyl-3-(phenylsulfonyl)-1H-indoles

  摘要：

  The discovery of a series of 4-aminoethyl-3-(phenylsulfonyl)-1H-indoles, dual acting norepinephrine reuptake inhibitors (NRIs) and 5-HT2A receptor antagonists, is described. The synthesis and structure-activity relationship (SAR) of this novel series of compounds is also presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.023

文献信息

• Sulfonyl Substituted 1H-Indoles as Ligands for the 5-Hydroxytryptamine Receptors
  申请人：McDevitt Robert E.

  公开号：US20070203120A1

  公开（公告）日：2007-08-30

  The present invention is directed to compounds of Formula I: which are modulators of the 5-hydroxtryptamine-6 and 5-hydroxytryptamine-2A receptors and which are inhibitors of norepinephrine reuptake. The compounds of the invention, and pharmaceutical composition thereof, are useful in the treatment of disorders related to or associated with the 5-hydroxytryptamine-6 and 5-hydroxtryptamine-2A receptors or with norepinephrine reuptake inhibition.

  本发明涉及式I的化合物：它们是5-羟色胺-6和5-羟色胺-2A受体的调节剂，同时也是去甲肾上腺素再摄取抑制剂。本发明的化合物及其制药组合物在治疗与5-羟色胺-6和5-羟色胺-2A受体或去甲肾上腺素再摄取抑制有关或相关的疾病方面是有用的。
• SULFONYL SUBSTITUTED 1H-INDOLES AS LIGANDS FOR THE 5-HYDROXYTRYPTAMINE RECEPTORS
  申请人：Wyeth

  公开号：EP1973876A2

  公开（公告）日：2008-10-01
• US7645752B2
  申请人：——

  公开号：US7645752B2

  公开（公告）日：2010-01-12
• [EN] SULFONYL SUBSTITUTED 1H-INDOLES AS LIGANDS FOR THE 5-HYDROXYTRYPTAMINE RECEPTORS<br/>[FR] 1H-INDOLES SUBSTITUES PAR UN GROUPE SULFONYLE EN TANT QUE LIGANDS POUR LES RECEPTEURS DE LA 5-HYDROXYTRYPTAMINE
  申请人：WYETH CORP

  公开号：WO2007084841A2

  公开（公告）日：2007-07-26

  [EN] The present invention is directed to compounds of Formula I: which are modulators of the 5-hydroxtryptamine-6 and 5-hydroxytryptamine-2A receptors and which are inhibitors of norepinephrine reuptake. The compounds of the invention, and pharmaceutical composition thereof, are useful in the treatment of disorders related to or associated with the 5-hydroxytryptamine-6 and 5- hydroxtryptamine-2A receptors or with norepinephrine reuptake inhibition.
  [FR] La présente invention concerne des composés répondant à la formule I : qui sont des modulateurs des récepteurs de la 5-hydroxtryptamine-6 et de la 5-hydroxytryptamine-2A et qui sont des inhibiteurs de recapture de la norépinéphrine. Les composés de la présente invention, et la composition pharmaceutique de ceux-ci, sont utiles dans le traitement de troubles se rapportant ou associés aux récepteurs de la 5-hydroxtryptamine-6 et de la 5-hydroxytryptamine-2A ou à l'inhibition de la recapture de la norépinéphrine.
• Dual acting norepinephrine reuptake inhibitors and 5-HT2A receptor antagonists: Identification, synthesis and activity of novel 4-aminoethyl-3-(phenylsulfonyl)-1H-indoles
  作者：Gavin D. Heffernan、Richard D. Coghlan、Eric S. Manas、Robert E. McDevitt、Yanfang Li、Paige E. Mahaney、Albert J. Robichaud、Christine Huselton、Peter Alfinito、Jenifer A. Bray、Scott A. Cosmi、Grace H. Johnston、Thomas Kenney、Elizabeth Koury、Richard C. Winneker、Darlene C. Deecher、Eugene J. Trybulski

  DOI：10.1016/j.bmc.2009.09.023

  日期：2009.11

  The discovery of a series of 4-aminoethyl-3-(phenylsulfonyl)-1H-indoles, dual acting norepinephrine reuptake inhibitors (NRIs) and 5-HT2A receptor antagonists, is described. The synthesis and structure-activity relationship (SAR) of this novel series of compounds is also presented. (C) 2009 Elsevier Ltd. All rights reserved.