3-Naphthalen-2-yl-1-(4-phenylpiperazin-1-yl)propan-1-one | 137517-41-0

• 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: 3-Naphthalen-2-yl-1-(4-phenylpiperazin-1-yl)propan-1-one
• CAS: 137517-41-0
• 化学式: C₂₃H₂₄N₂O
• 分子量: 344.456
• InChiKey: PGTKAJLYVSQXGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Naphthalen-2-yl-1-(4-phenylpiperazin-1-yl)propan-1-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 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
• 作为产物：
  描述：

  N-苯基哌嗪 、 3-萘-2-丙酸 在 氯甲酸乙酯 、 三乙胺 作用下， 生成 3-Naphthalen-2-yl-1-(4-phenylpiperazin-1-yl)propan-1-one
  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