1-(3-chlorophenyl)-4-phenylpropylpiperazine | 147429-39-8

• 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: 1-(3-chlorophenyl)-4-phenylpropylpiperazine
• 英文别名: 1-(3-Chloro-phenyl)-4-(3-phenyl-propyl)-piperazine；1-(3-chlorophenyl)-4-(3-phenylpropyl)piperazine
• CAS: 147429-39-8
• 化学式: C₁₉H₂₃ClN₂
• 分子量: 314.858
• InChiKey: LJDXYTBGUJEQSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  草酸 、 1-(3-chlorophenyl)-4-phenylpropylpiperazine 生成 1-(3-chlorophenyl)-4-phenylpropylpiperazine oxalate
  参考文献：
  名称：

  Chlorophenylpiperazine analogues as high affinity dopamine transporter ligands

  摘要：

  Selective sigma(2) ligands continue to be an active target for medications to attenuate the effects of psychostimulants. In the course of our studies to determine the optimal substituents in the sigma(2)-selective phenyl piperazines analogues with reduced activity at other neurotransmitter systems, we discovered that 1-(3-chlorophenyl)-4-phenethylpiperazine actually had preferentially increased affinity for dopamine transporters (DAT), yielding a highly selective DAT ligand. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.038
• 作为产物：
  描述：

  1-(3-氯苯基)哌嗪 在 dimethyl sulfide borane 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 生成 1-(3-chlorophenyl)-4-phenylpropylpiperazine
  参考文献：
  名称：

  Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity .sigma. ligands

  摘要：

  Sigma-receptors may represent an exciting new approach for the development of novel psychotherapeutic agents. Unfortunately, many of the commonly used sigma-ligands lack selectivity (e.g., many bind at phencyclidine or dopamine receptors) or suffer from other serious drawbacks. Recently, we described a series of 2-phenylaminoethanes that bind at sigma-receptors with high affinity and selectivity. Because there is evidence that 1-phenylpiperazines can structurally mimic the 2-phenylaminoethane moiety, we prepared a series of 1-phenylpiperazines and related analogues and incorporated structural features already shown to enhance the sigma-binding of the 2-phenylaminoethanes. Several of these derivatives bind at sigma-receptors with high affinity (K(i) = 1-10 nM) and lack appreciable affinity for phencyclidine and dopamine receptors. In as much as certain of these agents structurally resemble the high-affinity, but nonselective, sigma-ligand haloperidol, and because they bind with 10 times the affinity of haloperidol, we have apparently identified what appears to be the primary sigma-pharmacophore of that agent.

  DOI：

  10.1021/jm00116a003

文献信息

• SIGMA RECEPTOR LIGANDS AND THE USE THEREOF
  申请人：VIRGINIA COMMONWEALTH UNIVERSITY

  公开号：EP0507863A1

  公开（公告）日：1992-10-14
• EP0507863A4
  申请人：——

  公开号：EP0507863A4

  公开（公告）日：1993-07-07
• [EN] SIGMA RECEPTOR LIGANDS AND THE USE THEREOF
  申请人：——

  公开号：WO1991009594A1

  公开（公告）日：1991-07-11

  [EN] The invention relates to methods for the treatment of schizophrenia or other psychoses by administering a pharmaceutical composition comprising an effective amount of certain sigma receptor ligands to a patient in need of such treatment. The invention further relates to novel sigma receptor ligands having high binding to the sigma receptor and pharmaceutical compositions thereof.
  [FR] Procédés de traitement de la schizophrénie ou d'autres psychoses, par administration d'une composition pharmaceutique comprenant une quantité efficace de certains ligands de récepteur sigma, à un patient nécessitant un tel traitement. L'invention concerne également de nouveaux ligands de récepteur sigma, présentant une liaison élevée aux récepteurs sigma, ainsi que leurs compositions pharmaceutiques.
• Chlorophenylpiperazine analogues as high affinity dopamine transporter ligands
  作者：William C. Motel、Jason R. Healy、Eddy Viard、Buddy Pouw、Kelly E. Martin、Rae R. Matsumoto、Andrew Coop

  DOI：10.1016/j.bmcl.2013.09.038

  日期：2013.12

  Selective sigma(2) ligands continue to be an active target for medications to attenuate the effects of psychostimulants. In the course of our studies to determine the optimal substituents in the sigma(2)-selective phenyl piperazines analogues with reduced activity at other neurotransmitter systems, we discovered that 1-(3-chlorophenyl)-4-phenethylpiperazine actually had preferentially increased affinity for dopamine transporters (DAT), yielding a highly selective DAT ligand. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity .sigma. ligands
  作者：Richard A. Glennon、Mamoun Y. Yousif、Abd M. Ismaiel、Mahmoud B. El-Ashmawy、J. L. Herndon、James B. Fischer、Alfred C. Server、Kathleen J. Burke Howie

  DOI：10.1021/jm00116a003

  日期：1991.12

  Sigma-receptors may represent an exciting new approach for the development of novel psychotherapeutic agents. Unfortunately, many of the commonly used sigma-ligands lack selectivity (e.g., many bind at phencyclidine or dopamine receptors) or suffer from other serious drawbacks. Recently, we described a series of 2-phenylaminoethanes that bind at sigma-receptors with high affinity and selectivity. Because there is evidence that 1-phenylpiperazines can structurally mimic the 2-phenylaminoethane moiety, we prepared a series of 1-phenylpiperazines and related analogues and incorporated structural features already shown to enhance the sigma-binding of the 2-phenylaminoethanes. Several of these derivatives bind at sigma-receptors with high affinity (K(i) = 1-10 nM) and lack appreciable affinity for phencyclidine and dopamine receptors. In as much as certain of these agents structurally resemble the high-affinity, but nonselective, sigma-ligand haloperidol, and because they bind with 10 times the affinity of haloperidol, we have apparently identified what appears to be the primary sigma-pharmacophore of that agent.