1-[4-(3-Chloro-phenyl)-piperazin-1-yl]-2-phenyl-ethanone | 141511-18-4

• 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-[4-(3-Chloro-phenyl)-piperazin-1-yl]-2-phenyl-ethanone
• 英文别名: 1-[4-(3-chlorophenyl)piperazin-1-yl]-2-phenylethanone
• CAS: 141511-18-4
• 化学式: C₁₈H₁₉ClN₂O
• 分子量: 314.815
• InChiKey: BBUWDMCOPQCZQH-UHFFFAOYSA-N

物化性质

• 沸点：
  518.4±50.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  1-[4-(3-Chloro-phenyl)-piperazin-1-yl]-2-phenyl-ethanone 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 1-(3-chlorophenyl)-4-phenethylpiperazine
  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：

  苯乙酰氯 、 1-(3-氯苯基)哌嗪 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 1-[4-(3-Chloro-phenyl)-piperazin-1-yl]-2-phenyl-ethanone
  参考文献：
  名称：

  中枢神经系统制剂的结构活性关系研究。5.烃链对4-取代的1-（3-氯苯基）哌嗪对5-HT1A受体位点的亲和力的影响。

  摘要：

  研究了模型4-取代的1-（3-氯苯基）哌嗪12-31的烃链对其对5-HT1A受体位点的亲和力的影响。发现4-正烷基链的延长强烈增加了所研究化合物的5-HT1A亲和力。正己基衍生物20的亲和力达到最大值（Ki ＝ 2.67nM）。已表明1-芳基哌嗪的N-4取代基的疏水相互作用显着地促进了它们的5-HT1A亲和力。特异性结合常数定义为在生理条件下化合物的质子化物质的受体亲和力。Ki（AH +）的范围为1-3 x 10（-11）M是在5-HT1A受体位点上所研究化合物类别的特定亲和力极限。

  DOI：

  10.1021/jm00091a004

文献信息

• Structure-activity relationship studies of central nervous system (CNS) agents. 5. Effect of the hydrocarbon chain on the affinity of 4-substituted 1-(3-chlorophenyl)piperazines for 5-HT1A receptor sites
  作者：Jerzy L. Mokrosz、Marzena Pietrasiewicz、Beata Duszynska、Marek T. Cegla

  DOI：10.1021/jm00091a004

  日期：1992.6

  contribute to their 5-HT1A affinity. The specific binding constant was defined as the receptor affinity of the protonated species of compounds under physiological conditions. The range of Ki(AH+) = 1 - 3 x 10(-11) M is a specific affinity limit of the investigated class of compounds at the 5-HT1A receptor sites.

  研究了模型4-取代的1-（3-氯苯基）哌嗪12-31的烃链对其对5-HT1A受体位点的亲和力的影响。发现4-正烷基链的延长强烈增加了所研究化合物的5-HT1A亲和力。正己基衍生物20的亲和力达到最大值（Ki ＝ 2.67nM）。已表明1-芳基哌嗪的N-4取代基的疏水相互作用显着地促进了它们的5-HT1A亲和力。特异性结合常数定义为在生理条件下化合物的质子化物质的受体亲和力。Ki（AH +）的范围为1-3 x 10（-11）M是在5-HT1A受体位点上所研究化合物类别的特定亲和力极限。
• 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.