4-[3-(4-chlorophenoxy)propoxy]-2-nitrophenylamine | 875923-72-1

• 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: 4-[3-(4-chlorophenoxy)propoxy]-2-nitrophenylamine
• 英文别名: 4-[3-(4-chlorophenoxy)propoxy]-2-nitroaniline
• CAS: 875923-72-1
• 化学式: C₁₅H₁₅ClN₂O₄
• 分子量: 322.748
• InChiKey: RISWMTAPUARVQG-UHFFFAOYSA-N

物化性质

• 熔点：
  98-101 °C
• 沸点：
  506.7±40.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  87.62
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-[3-(4-chlorophenoxy)propoxy]-2-nitrophenylamine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 5(6)-[3-(p-chlorophenoxy)propoxy]-2-aminobenzimidazole
  参考文献：
  名称：

  Synthesis and biological evaluation of new non-imidazole H3-receptor antagonists of the 2-aminobenzimidazole series

  摘要：

  A novel series of non-imidazole H-3-receptor antagonists was developed, by chemical modification of a potent lead H-3-antagonist composed by an imidazole ring connected through an alkyl spacer to a 2-aminobenzimidazole moiety (e.g., 2-[[3-[4(5)-imidazolyl]propyl]amino]benzimidazole), previously reported by our research group. We investigated whether the removal of the imidazole ring could allow retaining high affinity for the H-3-receptor, thanks to the interactions undertaken by the 2-aminobenzimidazole moiety at the binding site. The imidazole ring of the lead was replaced by a basic piperidine or by a lipophilic p-chlorophenoxy substituent, modulating the spacer length from three to eight methylene groups; moreover, the substituents were moved to the 5(6) position of the benzimidazole nucleus. Within both the 2-alkylaminobenzimidazole series and the 5(6)-alkoxy-2-amino-benzimidazole one, the greatest H-3-receptor affinity was obtained for the piperidine-substituted compounds, while the presence of the p-chlorophenoxy group resulted in a drop in affinity. The optimal chain length was different in the two series. Even if the new compounds did not reach the high receptor affinity shown by the imidazole-containing lead compound, it was possible to get good H-3-antagonist potencies with 2-aminobenzimidazoles having a tertiary amino group at appropriate distance. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.063
• 作为产物：
  描述：

  N-[4-(3-chloropropoxy)-2-nitrophenyl]acetamide 在 氢氧化钾 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 4-[3-(4-chlorophenoxy)propoxy]-2-nitrophenylamine
  参考文献：
  名称：

  Synthesis and biological evaluation of new non-imidazole H3-receptor antagonists of the 2-aminobenzimidazole series

  摘要：

  A novel series of non-imidazole H-3-receptor antagonists was developed, by chemical modification of a potent lead H-3-antagonist composed by an imidazole ring connected through an alkyl spacer to a 2-aminobenzimidazole moiety (e.g., 2-[[3-[4(5)-imidazolyl]propyl]amino]benzimidazole), previously reported by our research group. We investigated whether the removal of the imidazole ring could allow retaining high affinity for the H-3-receptor, thanks to the interactions undertaken by the 2-aminobenzimidazole moiety at the binding site. The imidazole ring of the lead was replaced by a basic piperidine or by a lipophilic p-chlorophenoxy substituent, modulating the spacer length from three to eight methylene groups; moreover, the substituents were moved to the 5(6) position of the benzimidazole nucleus. Within both the 2-alkylaminobenzimidazole series and the 5(6)-alkoxy-2-amino-benzimidazole one, the greatest H-3-receptor affinity was obtained for the piperidine-substituted compounds, while the presence of the p-chlorophenoxy group resulted in a drop in affinity. The optimal chain length was different in the two series. Even if the new compounds did not reach the high receptor affinity shown by the imidazole-containing lead compound, it was possible to get good H-3-antagonist potencies with 2-aminobenzimidazoles having a tertiary amino group at appropriate distance. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.063