1-(4-chlorobutyl)-2-nitroaniline | 271581-56-7

• 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-(4-chlorobutyl)-2-nitroaniline
• 英文别名: N-(4-chlorobutyl)-2-nitroaniline
• CAS: 271581-56-7
• 化学式: C₁₀H₁₃ClN₂O₂
• 分子量: 228.678
• InChiKey: DMRPAMXZJMPPAP-UHFFFAOYSA-N

物化性质

• 沸点：
  383.6±27.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-chlorobutyl)-2-nitroaniline 在 镍 氢气 、 potassium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 37.0h， 生成 1-[4-(4-Benzyl-piperidin-1-yl)-butyl]-1,3-dihydro-benzoimidazol-2-one
  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：

  1-溴-4-氯丁烷 、 2-硝基苯胺 在 sodium hydride 作用下， 反应 7.0h， 以44%的产率得到1-(4-chlorobutyl)-2-nitroaniline
  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

文献信息

• Subtype-Selective <i>N</i>-Methyl-<scp>d</scp>-aspartate Receptor Antagonists:  Benzimidazalone and Hydantoin as Phenol Replacements
  作者：Robert M. Schelkun、Po-wai Yuen、Kevin Serpa、Leonard T. Meltzer、Lawrence D. Wise、Edward R. Whittemore、Richard M. Woodward

  DOI：10.1021/jm990537r

  日期：2000.5.1

  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.