2-(3,4-Dichloro-phenyl)-1H-benzoimidazole-5-carboxylic acid ethyl ester | 870114-99-1

• 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: 2-(3,4-Dichloro-phenyl)-1H-benzoimidazole-5-carboxylic acid ethyl ester
• 英文别名: ethyl 2-(3,4-dichlorophenyl)-3H-benzimidazole-5-carboxylate
• CAS: 870114-99-1
• 化学式: C₁₆H₁₂Cl₂N₂O₂
• 分子量: 335.189
• InChiKey: SPRWWWDQQQOZHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,4-Dichloro-phenyl)-1H-benzoimidazole-5-carboxylic acid ethyl ester 在 盐酸 、 氯化亚砜 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 5.5h， 生成 2-(3,4-dichlorophenyl)-N-[2-(1,4,5,6-tetrahydropyrimidin-2-yl)ethyl]-1H-benzimidazole-5-carbox-amide
  参考文献：
  名称：

  Synthesis and Potent In vitro Activity of Novel 1H-Benzimidazoles as Anti-MRSA Agents

  摘要：

  A new class of 1H‐benzimidazolecarboxamidines was synthesized and evaluated for in vitro antibacterial and antifungal activities, including drug‐resistant bacterial strains. The most potent compound (32) has the same ratio of anti‐MRSA activity as Vancomycin (minimal inhibitory concentrations value 0.78 μg/mL). The mechanism of action for 1H‐benzimidazolecarboxamidine appears to be different from existing antibacterial agents. These compounds have potential for development as a new class of potent anti‐MRSA agent.

  DOI：

  10.1111/j.1747-0285.2012.01393.x
• 作为产物：
  描述：

  Sodium; (3,4-dichloro-phenyl)-hydroxy-methanesulfonate 、 3,4-二氨基苯甲酸乙酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以85%的产率得到2-(3,4-Dichloro-phenyl)-1H-benzoimidazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and potent antibacterial activity against MRSA of some novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5-carboxamidines

  摘要：

  A series of 28 novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5-carboxamidine derivatives were synthesized and evaluated for in vitro antibacterial activities against Staphylococcus aureus and methicillin resistant S. aureus (MRSA) by the tube dilution method. The results showed that compounds 45-46 and 55-57, having 3,4-dichloro substituted phenyl at the position C-2, of N-bulky alkyl substituted benzimidazolecarboxamidines exhibited the greatest activity with MIC values of 1.56-0.39 mu g/ml. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.05.002

文献信息

• Synthesis and potent antibacterial activity against MRSA of some novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5-carboxamidines
  作者：Hakan Göker、Seçkin Özden、Sulhiye Yıldız、David W. Boykin

  DOI：10.1016/j.ejmech.2005.05.002

  日期：2005.10

  A series of 28 novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5-carboxamidine derivatives were synthesized and evaluated for in vitro antibacterial activities against Staphylococcus aureus and methicillin resistant S. aureus (MRSA) by the tube dilution method. The results showed that compounds 45-46 and 55-57, having 3,4-dichloro substituted phenyl at the position C-2, of N-bulky alkyl substituted benzimidazolecarboxamidines exhibited the greatest activity with MIC values of 1.56-0.39 mu g/ml. (c) 2005 Elsevier SAS. All rights reserved.
• Synthesis and Potent In vitro Activity of Novel 1H-Benzimidazoles as Anti-MRSA Agents
  作者：Hacer Karataş、Mehmet Alp、Sulhiye Yıldız、Hakan Göker

  DOI：10.1111/j.1747-0285.2012.01393.x

  日期：2012.8

  A new class of 1H‐benzimidazolecarboxamidines was synthesized and evaluated for in vitro antibacterial and antifungal activities, including drug‐resistant bacterial strains. The most potent compound (32) has the same ratio of anti‐MRSA activity as Vancomycin (minimal inhibitory concentrations value 0.78 μg/mL). The mechanism of action for 1H‐benzimidazolecarboxamidine appears to be different from existing antibacterial agents. These compounds have potential for development as a new class of potent anti‐MRSA agent.