4-hydroxy-4-phenyl-1-(3-phenylpropyl)piperidine | 147429-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-hydroxy-4-phenyl-1-(3-phenylpropyl)piperidine
• 英文别名: 4-Phenyl-1-(3-phenylpropyl)piperidin-4-ol
• CAS: 147429-41-2
• 化学式: C₂₀H₂₅NO
• 分子量: 295.425
• InChiKey: ZZUJERGWKSXINO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯丙醛 、 4-苯基-4-羟基哌啶 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-hydroxy-4-phenyl-1-(3-phenylpropyl)piperidine
  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
• US6057371A
  申请人：——

  公开号：US6057371A

  公开（公告）日：2000-05-02
• [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.
• 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.