3-(4-benzylpiperazin-1-ylmethyl)-3-benzoylpropionic acid | 99877-13-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-benzylpiperazin-1-ylmethyl)-3-benzoylpropionic acid
• 英文别名: 3-[(4-benzylpiperazin-1-ium-1-yl)methyl]-4-oxo-4-phenylbutanoate
• CAS: 99877-13-1
• 化学式: C₂₂H₂₆N₂O₃
• 分子量: 366.46
• InChiKey: ZJGSPOOYSJSOMV-UHFFFAOYSA-N

物化性质

• 熔点：
  155-158 °C(Solv: ethanol (64-17-5))
• 沸点：
  564.5±50.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-benzylpiperazin-1-ylmethyl)-3-benzoylpropionic acid 在 ammonium hydroxide 、 溴 、 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 4-[(4-benzylpiperazin-1-yl)methyl]-6-chloro-3-phenylpyridazine
  参考文献：
  名称：

  Ravina; Garcia Mera; Santana, European Journal of Medicinal Chemistry, 1985, vol. 20, # 5, p. 475 - 479

  摘要：

  DOI：
• 作为产物：
  描述：

  聚合甲醛 、 1-苄基哌嗪 、 3-苯丙烯溴酸酯 以 甲醇 、 水 为溶剂， 反应 0.25h， 以49%的产率得到3-(4-benzylpiperazin-1-ylmethyl)-3-benzoylpropionic acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 1-Aralkyl-4-Benzylpiperidine and 1-Aralkyl-4-Benzylpiperazine Derivatives as Potent σ Ligands

  摘要：

  In the attempt to define more accurately structure-affinity relationships for sigma(1) and sigma(2) ligands, we synthesized and tested on sigma subtype receptors a series of aralkyl derivatives of 4-benzylpiperidine, in which the effect of modifications on the aralkyl moiety was studied in a systematic way. The affinity of the compounds here described varied to a great extent, with a sigma(2)/sigma(1), selectivity ranging from 0.1 to 9. Thus, to confirm the ability of the piperazine derivative to bind to sigma(1) receptors in a different way than piperidines, we synthesized and tested a series of piperazine compounds; the comparison of their affinity with that of the corresponding piperidines strongly supports the possibility of a different binding mode. While the compounds here described are on the whole selective for a vs serotonin 5-HT1A and dopamine D-2 receptors, 9aa, 9ba and 9ab possess a remarkable affinity for both a and 5-HT1A receptors, with K-i in the nanomolar range, and are selective with respect to D2 receptors. They displayed also a partial agonist profile in a human 5-HT1A [S-35]GTPgammaS binding assay, suggesting their potential use as atypical antipsychotic agents.

  DOI：

  10.1021/jm049433t

文献信息

• RAVINA, E.;GARCIA, MERA, G.;SANTANA, L.;ORALLO, F.;CALLEJA, J. M., EUR. J. MED. CHEM., 1985, 20, N 5, 475-479
  作者：RAVINA, E.、GARCIA, MERA, G.、SANTANA, L.、ORALLO, F.、CALLEJA, J. M.

  DOI：——

  日期：——
• Synthesis and Structure−Activity Relationships of 1-Aralkyl-4-Benzylpiperidine and 1-Aralkyl-4-Benzylpiperazine Derivatives as Potent σ Ligands
  作者：Luca Costantino、Francesca Gandolfi、Claudia Sorbi、Silvia Franchini、Orazio Prezzavento、Franco Vittorio、Giuseppe Ronsisvalle、Amedeo Leonardi、Elena Poggesi、Livio Brasili

  DOI：10.1021/jm049433t

  日期：2005.1.1

  In the attempt to define more accurately structure-affinity relationships for sigma(1) and sigma(2) ligands, we synthesized and tested on sigma subtype receptors a series of aralkyl derivatives of 4-benzylpiperidine, in which the effect of modifications on the aralkyl moiety was studied in a systematic way. The affinity of the compounds here described varied to a great extent, with a sigma(2)/sigma(1), selectivity ranging from 0.1 to 9. Thus, to confirm the ability of the piperazine derivative to bind to sigma(1) receptors in a different way than piperidines, we synthesized and tested a series of piperazine compounds; the comparison of their affinity with that of the corresponding piperidines strongly supports the possibility of a different binding mode. While the compounds here described are on the whole selective for a vs serotonin 5-HT1A and dopamine D-2 receptors, 9aa, 9ba and 9ab possess a remarkable affinity for both a and 5-HT1A receptors, with K-i in the nanomolar range, and are selective with respect to D2 receptors. They displayed also a partial agonist profile in a human 5-HT1A [S-35]GTPgammaS binding assay, suggesting their potential use as atypical antipsychotic agents.
• Ravina; Garcia Mera; Santana, European Journal of Medicinal Chemistry, 1985, vol. 20, # 5, p. 475 - 479
  作者：Ravina、Garcia Mera、Santana、et al.

  DOI：——

  日期：——