1-phenyl-4-[3-(2-naphthyl)propyl]piperazine | 136534-58-2

• 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-phenyl-4-[3-(2-naphthyl)propyl]piperazine
• 英文别名: 1-(3-Naphthalen-2-yl-propyl)-4-phenyl-piperazine；1-(3-naphthalen-2-ylpropyl)-4-phenylpiperazine
• CAS: 136534-58-2
• 化学式: C₂₃H₂₆N₂
• 分子量: 330.473
• InChiKey: ZDMWBBFQNAAKPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-萘-2-丙酸 在 lithium aluminium tetrahydride 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 1-phenyl-4-[3-(2-naphthyl)propyl]piperazine
  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：EP0591426A1

  公开（公告）日：1994-04-13
• [EN] SIGMA RECEPTOR LIGANDS AND THE USE THEREOF
  申请人：——

  公开号：WO1993000313A2

  公开（公告）日：1993-01-07

  [EN] The invention relates to methods for the treatment of central nervous system disorders, gastrointestinal disorders, drug abuse, angina, migraine, hypertension and depression 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. Unexpectedly, certain of the sigma receptor ligands of the present invention have selectivity for the sigma receptor over the DA, PCP and 5-HT1A receptors.
  [FR] L'invention concerne des procédés de traitement des troubles du sytème nerveux central, des troubles gastro-intestinaux, la prise abusive de médicaments, l'engine, la migraine, l'hypertension et la dépression, en administrant une composition pharmaceutique comprenant une quantité efficace de certains ligands de récepteurs sigma à un patient ayant besoin d'un tel traitement. L'invention concerne en outre de nouveaux ligands de récepteur sigma ayant un pouvoir élevé de liaison sur le récepteur sigma ainsi que leurs compositions pharmaceutiques. De manière inattendue, certains ligands de récepteur sigma de la présente invention font preuve de sélectivité pour le récepteur sigma au détriment des récepteurs DA,PCP et 5-HT1A.
• 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.