6-(1H-benzo[d]imidazol-2-yl)-2-(benzylideneamino)-4-(4-methoxyphenyl)nicotinonitrile | 1456802-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 6-(1H-benzo[d]imidazol-2-yl)-2-(benzylideneamino)-4-(4-methoxyphenyl)nicotinonitrile
• CAS: 1456802-39-3
• 化学式: C₂₇H₁₉N₅O
• 分子量: 429.481
• InChiKey: VOFSMQGFDINXAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  86.95
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-(1H-benzo[d]imidazol-2-yl)-2-(benzylideneamino)-4-(4-methoxyphenyl)nicotinonitrile 、 氯乙酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.0h， 以59%的产率得到6-(1H-benzo[d]imidazol-2-yl)-2-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-4-(4-methoxyphenyl)nicotinonitrile
  参考文献：
  名称：

  Synthesis, antimicrobial and cytotoxic activity of 2-azetidinone derivatives of pyridyl benzimidazoles

  摘要：

  In the present study, a series of novel 6-(1H-benzo[d]imidazol-2-yl)-2-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-4-(aryl)nicotinonitriles 6a-o were efficiently synthesized and evaluated for their in vitro antibacterial activity against Gram-positive (Staphylococcus aureus and Streptococcus pyogenes), Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria and fungal (Candida albicans, Aspergillus niger and Aspergillus clavatus) strains. The results of antimicrobial study revealed that compounds 6b, 6c, 6d, 6h and 6i exhibited substantial antibacterial activity while compounds 6c and 6h emerged as the most potent antifungal agents compared to the standard drugs chloramphenicol and ketoconazole, respectively. From the standpoint of SAR studies, it was observed that the presence of electron-withdrawing groups remarkably enhances the antibacterial activity of newly synthesized compounds. Further, the results of preliminary MTT cytotoxicity studies on HeLa cells suggested that potent antimicrobial activity of 6b, 6c, 6d, 6h and 6i is accompanied by low level of cytotoxic concentrations. All the newly synthesized analogues were characterized by IR, H-1 NMR, C-13 NMR and mass spectral data.

  DOI：

  10.1007/s00044-013-0775-1
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 ammonium acetate 、 potassium hydroxide 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 26.0h， 生成 6-(1H-benzo[d]imidazol-2-yl)-2-(benzylideneamino)-4-(4-methoxyphenyl)nicotinonitrile
  参考文献：
  名称：

  Synthesis, antimicrobial and cytotoxic activity of 2-azetidinone derivatives of pyridyl benzimidazoles

  摘要：

  In the present study, a series of novel 6-(1H-benzo[d]imidazol-2-yl)-2-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-4-(aryl)nicotinonitriles 6a-o were efficiently synthesized and evaluated for their in vitro antibacterial activity against Gram-positive (Staphylococcus aureus and Streptococcus pyogenes), Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria and fungal (Candida albicans, Aspergillus niger and Aspergillus clavatus) strains. The results of antimicrobial study revealed that compounds 6b, 6c, 6d, 6h and 6i exhibited substantial antibacterial activity while compounds 6c and 6h emerged as the most potent antifungal agents compared to the standard drugs chloramphenicol and ketoconazole, respectively. From the standpoint of SAR studies, it was observed that the presence of electron-withdrawing groups remarkably enhances the antibacterial activity of newly synthesized compounds. Further, the results of preliminary MTT cytotoxicity studies on HeLa cells suggested that potent antimicrobial activity of 6b, 6c, 6d, 6h and 6i is accompanied by low level of cytotoxic concentrations. All the newly synthesized analogues were characterized by IR, H-1 NMR, C-13 NMR and mass spectral data.

  DOI：

  10.1007/s00044-013-0775-1