2-nitro-4-{2-[4-(4-chlorophenyl)piperazin-1-yl]ethoxy}aniline | 856400-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-nitro-4-{2-[4-(4-chlorophenyl)piperazin-1-yl]ethoxy}aniline
• 英文别名: 4-[2-(4-(4-chlorophenyl)piperazin-1-yl)-ethoxy]-2-nitrophenylamine；4-[2-[4-(4-Chlorophenyl)piperazin-1-yl]ethoxy]-2-nitroaniline
• CAS: 856400-27-6
• 化学式: C₁₈H₂₁ClN₄O₃
• 分子量: 376.843
• InChiKey: ZTGFMFYHBNIZTD-UHFFFAOYSA-N

物化性质

• 熔点：
  106 °C(Solv: isopropanol (67-63-0))
• 沸点：
  586.0±50.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-nitro-4-{2-[4-(4-chlorophenyl)piperazin-1-yl]ethoxy}aniline 在 Ra-Ni 、 一水合肼 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 4-[2-(4-(4-chlorophenyl)piperazin-1-yl)-ethoxy]-benzene-1,2-diamine
  参考文献：
  名称：

  Synthesis, dopamine D2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs

  摘要：

  5-[3-(4-Arylpiperazin-1-yl)propyl]-1H-benzimidazoles and 5-[2-(4-aryipiperazin-1-yl)ethoxy]-1H-benzimidazoles were synthesized and their affinity for the D-1, D-2 and 5-HT1A, receptors examined. They expressed a rather high affinity for the D-2 doparnine receptor. The main features of ligand-D-2 receptor interactions revealed by docking analyses were: salt bridge between piperazine ring protonated N-1 and Asp 86, hydrogen bonds of ligand bezimidazole part with Ser 141, Ser 122 and His 189, edge-to-face interactions of arylpiperazine aromatic ring with Phe 178, Tyr 216 and Trp 182 and hydrogen bond between ethereal oxygen in ethylenoxy ligands and hydrogen of Phe 185 or Trp 115. The most active 5-{2-[4-(2-methoxyphenyl)-piperazin-1-yl]ethoxy}-1,3-di hydro-2H-benzimidazole-2-thione (27) has a maximal number of attractive interactions. A satisfactory correlation between docking of the compounds into the D-2 receptor and competition binding results was observed. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.10.006
• 作为产物：
  描述：

  2-氯乙基 4-硝基苯基醚 在 盐酸 、 硝酸 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 2-nitro-4-{2-[4-(4-chlorophenyl)piperazin-1-yl]ethoxy}aniline
  参考文献：
  名称：

  Synthesis, dopamine D2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs

  摘要：

  5-[3-(4-Arylpiperazin-1-yl)propyl]-1H-benzimidazoles and 5-[2-(4-aryipiperazin-1-yl)ethoxy]-1H-benzimidazoles were synthesized and their affinity for the D-1, D-2 and 5-HT1A, receptors examined. They expressed a rather high affinity for the D-2 doparnine receptor. The main features of ligand-D-2 receptor interactions revealed by docking analyses were: salt bridge between piperazine ring protonated N-1 and Asp 86, hydrogen bonds of ligand bezimidazole part with Ser 141, Ser 122 and His 189, edge-to-face interactions of arylpiperazine aromatic ring with Phe 178, Tyr 216 and Trp 182 and hydrogen bond between ethereal oxygen in ethylenoxy ligands and hydrogen of Phe 185 or Trp 115. The most active 5-{2-[4-(2-methoxyphenyl)-piperazin-1-yl]ethoxy}-1,3-di hydro-2H-benzimidazole-2-thione (27) has a maximal number of attractive interactions. A satisfactory correlation between docking of the compounds into the D-2 receptor and competition binding results was observed. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.10.006

文献信息

• Synthesis, dopamine D2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs
  作者：V. Šukalović、Deana Andrić、G. Roglić、Sladjana Kostić-Rajačić、A. Schrattenholz、V. Šoškić

  DOI：10.1016/j.ejmech.2004.10.006

  日期：2005.5

  5-[3-(4-Arylpiperazin-1-yl)propyl]-1H-benzimidazoles and 5-[2-(4-aryipiperazin-1-yl)ethoxy]-1H-benzimidazoles were synthesized and their affinity for the D-1, D-2 and 5-HT1A, receptors examined. They expressed a rather high affinity for the D-2 doparnine receptor. The main features of ligand-D-2 receptor interactions revealed by docking analyses were: salt bridge between piperazine ring protonated N-1 and Asp 86, hydrogen bonds of ligand bezimidazole part with Ser 141, Ser 122 and His 189, edge-to-face interactions of arylpiperazine aromatic ring with Phe 178, Tyr 216 and Trp 182 and hydrogen bond between ethereal oxygen in ethylenoxy ligands and hydrogen of Phe 185 or Trp 115. The most active 5-2-[4-(2-methoxyphenyl)-piperazin-1-yl]ethoxy}-1,3-di hydro-2H-benzimidazole-2-thione (27) has a maximal number of attractive interactions. A satisfactory correlation between docking of the compounds into the D-2 receptor and competition binding results was observed. (c) 2005 Elsevier SAS. All rights reserved.