4-[2-(4-phenyl-1-piperazinyl)ethyl]cyclohexanone | 189153-16-0

• 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: 4-[2-(4-phenyl-1-piperazinyl)ethyl]cyclohexanone
• 英文别名: 4-[2-(4-Phenylpiperazin-1-yl)ethyl]cyclohexan-1-one
• CAS: 189153-16-0
• 化学式: C₁₈H₂₆N₂O
• 分子量: 286.417
• InChiKey: GQPRRTKPIBKYQK-UHFFFAOYSA-N

物化性质

• 沸点：
  433.2±30.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[2-(4-phenyl-1-piperazinyl)ethyl]cyclohexanone 在 盐酸 、 ammonium acetate 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 82.0h， 生成 4-[2-(4-Phenyl-piperazin-1-yl)-ethyl]-cyclohexylamine
  参考文献：
  名称：

  Aminopyrimidines with High Affinity for Both Serotonin and Dopamine Receptors

  摘要：

  A series of {4-[2-(4-arylpiperazin-1-yl)alkyl]cyclohexyl}pyrimidin-2-ylamines was prepared and found to have receptor binding affinity for D2 and D3 dopamine (DA) receptors and serotonin 5-HT1A receptors. The structural contributions to D2/D3 and 5-HT1A receptor binding of the aminopyrimidine, cycloalkyl, and phenylpiperazine portions of the molecule were examined. From these studies compounds 14, 39, 42, 43, having potent affinity for both DA D2 and 5-HT1A receptors, were evaluated for intrinsic activity at these receptors, in vitro and in vivo. Compound 14 (PD 158771) had a profile indicative of partial agonist activity at both D2 and 5-HT1A receptors causing partially decreased synthesis of the neurotransmitters DA and 5-HT and their metabolites. This compound has a profile in behavioral tests that is predictive of antipsychotic activity, suggesting that mixed, partial agonists such as 14 may have utility as antipsychotic agents with increased efficacy and decreased side effects.

  DOI：

  10.1021/jm9707378
• 作为产物：
  描述：

  (1,4-二噁螺[4,5]-8-癸基)-乙酸乙酯 在 盐酸 、 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 生成 4-[2-(4-phenyl-1-piperazinyl)ethyl]cyclohexanone
  参考文献：
  名称：

  Novel cyclohexyl amides as potent and selective D3 dopamine receptor ligands

  摘要：

  The dopamine D-3 receptor is an attractive target for the treatment of schizophrenia. We identified PD137557 (V) as a ligand for the D-2 receptor and desired to prepare a selective D3 compound. SAR studies involving different amides and different phenyl piperazines have led to the discovery of 8a and 8c as selective D-3 receptor ligands. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00443-5

文献信息

• Novel cyclohexyl amides as potent and selective D3 dopamine receptor ligands
  作者：Thomas R. Belliotti、Suzanne R. Kesten、John R. Rubin、David J. Wustrow、Lynn M. Georgic、Kim T. Zoski、Hyacinth C. Akunne、Lawrence D. Wise

  DOI：10.1016/s0960-894x(97)00443-5

  日期：1997.9

  The dopamine D-3 receptor is an attractive target for the treatment of schizophrenia. We identified PD137557 (V) as a ligand for the D-2 receptor and desired to prepare a selective D3 compound. SAR studies involving different amides and different phenyl piperazines have led to the discovery of 8a and 8c as selective D-3 receptor ligands. (C) 1997 Elsevier Science Ltd.
• Aminopyrimidines with High Affinity for Both Serotonin and Dopamine Receptors
  作者：David Wustrow、Thomas Belliotti、Shelly Glase、Suzanne Ross Kesten、Don Johnson、Norman Colbry、Ronald Rubin、Anthony Blackburn、Hyacinth Akunne、Ann Corbin、M. Duff Davis、Lynn Georgic、Steven Whetzel、Kim Zoski、Thomas Heffner、Thomas Pugsley、Lawrence Wise

  DOI：10.1021/jm9707378

  日期：1998.2.1

  A series of 4-[2-(4-arylpiperazin-1-yl)alkyl]cyclohexyl}pyrimidin-2-ylamines was prepared and found to have receptor binding affinity for D2 and D3 dopamine (DA) receptors and serotonin 5-HT1A receptors. The structural contributions to D2/D3 and 5-HT1A receptor binding of the aminopyrimidine, cycloalkyl, and phenylpiperazine portions of the molecule were examined. From these studies compounds 14, 39, 42, 43, having potent affinity for both DA D2 and 5-HT1A receptors, were evaluated for intrinsic activity at these receptors, in vitro and in vivo. Compound 14 (PD 158771) had a profile indicative of partial agonist activity at both D2 and 5-HT1A receptors causing partially decreased synthesis of the neurotransmitters DA and 5-HT and their metabolites. This compound has a profile in behavioral tests that is predictive of antipsychotic activity, suggesting that mixed, partial agonists such as 14 may have utility as antipsychotic agents with increased efficacy and decreased side effects.