4-({1-[2-(2,4-difluorophenyl)ethyl]-4-fluoropiperidin-4-yl}sulfonyl)benzonitrile | 797749-91-8

• 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: 4-({1-[2-(2,4-difluorophenyl)ethyl]-4-fluoropiperidin-4-yl}sulfonyl)benzonitrile
• 英文别名: 4-({1-[2-(2,4-Difluorophenyl)ethyl]-4-fluoropiperidine-4-yl}sulfonyl)benzonitrile；4-[1-[2-(2,4-difluorophenyl)ethyl]-4-fluoropiperidin-4-yl]sulfonylbenzonitrile
• CAS: 797749-91-8
• 化学式: C₂₀H₁₉F₃N₂O₂S
• 分子量: 408.444
• InChiKey: RPBDTRSLAXVOEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-({1-[2-(2,4-difluorophenyl)ethyl]-4-fluoropiperidin-4-yl}sulfonyl)benzonitrile 在 水 、 双氧水 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 生成 4-({1-[2-(2,4-difluorophenyl)ethyl]-4-fluoropiperidin-4-yl}sulfonyl)benzamide
  参考文献：
  名称：

  [EN] 4-ARYLSULPHONYLPIPERIDINE DERIVATIVES FOR ANTAGONISM OF THE 5-HT2A RECEPTOR
  [FR] DERIVES DE 4-ARYLSULPHONYLPIPERIDINE POUR L'ANTAGONISME DU RECEPTEUR DE 5-HT2A

  摘要：

  式(I)的化合物是5-HT2A受体的选择性拮抗剂，因此在治疗中枢神经系统的不良症状，如睡眠障碍和精神分裂症方面具有用处。

  公开号：

  WO2004101518A1
• 作为产物：
  描述：

  1-(2,4-difluorophenethyl)-4-((4-fluorophenyl)sulfonyl)piperidine 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 4-({1-[2-(2,4-difluorophenyl)ethyl]-4-fluoropiperidin-4-yl}sulfonyl)benzonitrile
  参考文献：
  名称：

  4-Fluorosulfonylpiperidines: Selective 5-HT2A ligands for the treatment of insomnia

  摘要：

  Incorporation of fluorine at the 4-position of an existing series of sulfonyl piperidine 5-HT2A antagonists gave compounds with increased selectivity over the IKr potassium channel. This work led to the identification of 3b, a compound that gave no increase in QT(c) in the anesthetized dog up to plasma levels as high as 148 mu M. Furthermore, 3b has been shown to increase slow-wave sleep bout duration and to decrease the number of awakenings in rats, indicating the potential utility of 5-HT2A antagonists in the treatment of insomnia. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.104

文献信息

• 4-Arylsulphonylpiperidine derivatives for antagonism of the 5-ht2a receptor
  申请人：Gilligan Myra

  公开号：US20060211735A1

  公开（公告）日：2006-09-21

  Compounds of formula (I): are selective antagonists of the 5-HT 2A receptor, and hence are useful in treatment of adverse conditions at the central nervous system, such as sleep disorders and schizophrenia.

  公式为(I)的化合物是5-HT2A受体的选择性拮抗剂，因此可用于治疗中枢神经系统的不良症状，如睡眠障碍和精神分裂症。
• 4-ARYLSULPHONYLPIPERIDINE DERIVATIVES FOR ANTAGONISM OF THE 5-HT2A RECEPTOR
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP1641756A1

  公开（公告）日：2006-04-05
• [EN] 4-ARYLSULPHONYLPIPERIDINE DERIVATIVES FOR ANTAGONISM OF THE 5-HT2A RECEPTOR<br/>[FR] DERIVES DE 4-ARYLSULPHONYLPIPERIDINE POUR L'ANTAGONISME DU RECEPTEUR DE 5-HT2A
  申请人：MERCK SHARP & DOHME

  公开号：WO2004101518A1

  公开（公告）日：2004-11-25

  Compounds of formula (I): are selective antagonists of the 5-HT2A receptor, and hence are useful in treatment of adverse conditions at the central nervous system, such as sleep disorders and schizophrenia.

  式(I)的化合物是5-HT2A受体的选择性拮抗剂，因此在治疗中枢神经系统的不良症状，如睡眠障碍和精神分裂症方面具有用处。
• 4-Fluorosulfonylpiperidines: Selective 5-HT2A ligands for the treatment of insomnia
  作者：L. Rebecca Fish、Myra T. Gilligan、Alexander C. Humphries、Magnus Ivarsson、Tammy Ladduwahetty、Kevin J. Merchant、Desmond O’Connor、Smita Patel、Elisabeth Philipps、Hugo M. Vargas、Peter H. Hutson、Angus M. MacLeod

  DOI：10.1016/j.bmcl.2005.05.104

  日期：2005.8

  Incorporation of fluorine at the 4-position of an existing series of sulfonyl piperidine 5-HT2A antagonists gave compounds with increased selectivity over the IKr potassium channel. This work led to the identification of 3b, a compound that gave no increase in QT(c) in the anesthetized dog up to plasma levels as high as 148 mu M. Furthermore, 3b has been shown to increase slow-wave sleep bout duration and to decrease the number of awakenings in rats, indicating the potential utility of 5-HT2A antagonists in the treatment of insomnia. (c) 2005 Elsevier Ltd. All rights reserved.