1-(3-Nitrobenzyl)-4-(3-phenylpropyl)piperazine | 488801-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3-Nitrobenzyl)-4-(3-phenylpropyl)piperazine
• 英文别名: 1-[(3-nitrophenyl)methyl]-4-(3-phenylpropyl)piperazine
• CAS: 488801-02-1
• 化学式: C₂₀H₂₅N₃O₂
• 分子量: 339.437
• InChiKey: AQGMGOPOJDMNMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯基丙基哌嗪 、 3-硝基溴苄 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以70%的产率得到1-(3-Nitrobenzyl)-4-(3-phenylpropyl)piperazine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of N-(3-phenylpropyl)-N′-benzylpiperazines: Potent ligands for σ1 and σ2 receptors

  摘要：

  Ten N-(3-phenylpropyl)-N'-benzylpiperazines having different substituents on the benzyl moiety were synthesized and evaluated for sigma(1) and sigma(2) receptor binding. The sigma(1) affinities were 0.37-2.80 nM, sigma(2) affinities were 1.03-34.3 nM, and selectivities, as sigma(2)/sigma(1) affinity ratios, ranged from 1.4 to 52. Three compounds tested in a phenytoin shift binding assay profiled as probable a, antagonists. Quantitative structure-activity relationships depended on pi(x), MR or E-S and Hammett sigma values. The hydrophobicity term is negative for sigma(1) binding but positive for sigma(2) binding, indicating a major difference between the pharmacophores. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.037

文献信息

• Synthesis and structure–activity relationships of N-(3-phenylpropyl)-N′-benzylpiperazines: Potent ligands for σ1 and σ2 receptors
  作者：Roger I. Nahas、John R. Lever、Susan Z. Lever

  DOI：10.1016/j.bmc.2007.10.037

  日期：2008.1

  Ten N-(3-phenylpropyl)-N'-benzylpiperazines having different substituents on the benzyl moiety were synthesized and evaluated for sigma(1) and sigma(2) receptor binding. The sigma(1) affinities were 0.37-2.80 nM, sigma(2) affinities were 1.03-34.3 nM, and selectivities, as sigma(2)/sigma(1) affinity ratios, ranged from 1.4 to 52. Three compounds tested in a phenytoin shift binding assay profiled as probable a, antagonists. Quantitative structure-activity relationships depended on pi(x), MR or E-S and Hammett sigma values. The hydrophobicity term is negative for sigma(1) binding but positive for sigma(2) binding, indicating a major difference between the pharmacophores. (c) 2007 Elsevier Ltd. All rights reserved.