1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-amino-4-(4-nitrophenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile | 1618096-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-amino-4-(4-nitrophenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile
• 英文别名: 1-((1-(1h-Benzo[d]imidazol-2-yl)ethylidene)amino)-6-amino-4-(4-nitrophenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile；2-amino-1-[1-(1H-benzimidazol-2-yl)ethylideneamino]-4-(4-nitrophenyl)-6-oxopyridine-3,5-dicarbonitrile
• CAS: 1618096-82-4
• 化学式: C₂₂H₁₄N₈O₃
• 分子量: 438.405
• InChiKey: ZAPUYNNHHIWZLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-amino-4-(4-nitrophenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile 、 对硝基苯甲醛 以 乙醇 为溶剂， 反应 5.0h， 以66%的产率得到1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((4-nitrobenzylidene)amino)-4-(4-nitrophenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  Synthesis, antibacterial and antitubercular activities of benzimidazole bearing substituted 2-pyridone motifs

  摘要：

  A series of benzimidazole bearing 2-pyridones 5a-r were synthesized and evaluated for their in vitro antibacterial and antitubercular activity. Further, all compounds were examined for their cytotoxic study on VERO cell line and characterized by well-known spectral techniques. It was observed that the compounds 5h, 5i, 5k, 5q and 5r were found to possess significant broad spectrum antibacterial activity (12.5-100 mu g/mL of MIC), while compounds 5g-5i, 5k and 5l proved to be the most potent antitubercular activity in range of 2.76-20.4 mu M of MIC at low level of cytotoxicity, indicating good selectivity. From SAR studies, lipophilic profile of compounds was remarkably vital for antibacterial activity, while MIC values of antitubercular activity could not be directly correlated with lipophilicity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.06.004
• 作为产物：
  描述：

  2-乙酰苯并咪唑 在 哌啶 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 6.0h， 生成 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-amino-4-(4-nitrophenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  Synthesis, antibacterial and antitubercular activities of benzimidazole bearing substituted 2-pyridone motifs

  摘要：

  A series of benzimidazole bearing 2-pyridones 5a-r were synthesized and evaluated for their in vitro antibacterial and antitubercular activity. Further, all compounds were examined for their cytotoxic study on VERO cell line and characterized by well-known spectral techniques. It was observed that the compounds 5h, 5i, 5k, 5q and 5r were found to possess significant broad spectrum antibacterial activity (12.5-100 mu g/mL of MIC), while compounds 5g-5i, 5k and 5l proved to be the most potent antitubercular activity in range of 2.76-20.4 mu M of MIC at low level of cytotoxicity, indicating good selectivity. From SAR studies, lipophilic profile of compounds was remarkably vital for antibacterial activity, while MIC values of antitubercular activity could not be directly correlated with lipophilicity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.06.004