[4-(4-benzylpiperidin-1-yl)butyl](2-nitrophenyl)amine | 271581-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: [4-(4-benzylpiperidin-1-yl)butyl](2-nitrophenyl)amine
• 英文别名: N-[4-(4-benzylpiperidin-1-yl)butyl]-2-nitroaniline
• CAS: 271581-62-5
• 化学式: C₂₂H₂₉N₃O₂
• 分子量: 367.491
• InChiKey: YNVHPPDNJKFMBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [4-(4-benzylpiperidin-1-yl)butyl](2-nitrophenyl)amine 在 镍 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 以100%的产率得到2-N-[4-(4-benzylpiperidin-1-yl)butyl]benzene-1,2-diamine
  参考文献：
  名称：

  Subtype-Selective N-Methyl-d-aspartate Receptor Antagonists:  Benzimidazalone and Hydantoin as Phenol Replacements

  摘要：

  Previous work in our laboratories investigating compounds with structural similarity to ifenprodil (5) and 6 (CP101,606) resulted in compound 7 as a potent and selective antagonist of the NR1/2B subtype of the NMDA receptors. Replacement of the phenol, group of 7 with a benzimidazalone group tethered by a three-carbon chain to 4-benzylpiperidine resulted in a slightly less active, but selective, compound. Lengthening the carbon tether resulted in a decrease in NR1/2B potency. Replacement of the phenol ring with a hydantoin resulted in weak antagonists. Compound 11a was one of the most potent NR1/2B antagonists from this study. Compound 11a also potentiated the effects of L-DOPA in a rat model of Parkinson's disease (the 6-hydroxydopamine-lesioned rat), dosed at 30 mg/kg orally.

  DOI：

  10.1021/jm990537r
• 作为产物：
  描述：

  2-硝基苯胺 在 sodium hydride 、 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 25.0h， 生成 [4-(4-benzylpiperidin-1-yl)butyl](2-nitrophenyl)amine
  参考文献：
  名称：

  Subtype-Selective N-Methyl-d-aspartate Receptor Antagonists:  Benzimidazalone and Hydantoin as Phenol Replacements

  摘要：

  Previous work in our laboratories investigating compounds with structural similarity to ifenprodil (5) and 6 (CP101,606) resulted in compound 7 as a potent and selective antagonist of the NR1/2B subtype of the NMDA receptors. Replacement of the phenol, group of 7 with a benzimidazalone group tethered by a three-carbon chain to 4-benzylpiperidine resulted in a slightly less active, but selective, compound. Lengthening the carbon tether resulted in a decrease in NR1/2B potency. Replacement of the phenol ring with a hydantoin resulted in weak antagonists. Compound 11a was one of the most potent NR1/2B antagonists from this study. Compound 11a also potentiated the effects of L-DOPA in a rat model of Parkinson's disease (the 6-hydroxydopamine-lesioned rat), dosed at 30 mg/kg orally.

  DOI：

  10.1021/jm990537r