2-(2,4-difluorophenyl)-5-fluoro-1H-benzimidazole

• 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-(2,4-difluorophenyl)-5-fluoro-1H-benzimidazole
• 英文别名: 2-(2,4-difluorophenyl)-6-fluoro-1H-benzimidazole
• 化学式: C₁₃H₇F₃N₂
• mdl: MFCD21369836
• 分子量: 248.207
• InChiKey: WRSFSHALGVIASA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氟-1,2-苯二胺 、 2,4-二氟苯甲醛 在 sodium metabisulfite 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以56%的产率得到2-(2,4-difluorophenyl)-5-fluoro-1H-benzimidazole
  参考文献：
  名称：

  Synthesis andIn VitroActivity of Polyhalogenated 2-phenylbenzimidazoles as a New Class of anti-MRSA and Anti-VRE Agents

  摘要：

  A series of novel polyhalogenated 2‐phenylbenzimidazoles have been synthesized and evaluated for in vitro antistaphylococcal activity against drug‐resistant bacterial strains (methicillin‐resistant Staphylococcus aureus, and vancomycin‐resistant Enterococcus faecium. Certain compounds inhibit bacterial growth perfectly. 11 was active than vancomycin (0.78 μg/mL) with the lowest MIC values with 0.19 μg/mL against methicillin‐resistant Staphylococcus aureus, 8 and 35 exhibited best inhibitory activity against vancomycin‐resistant Enterococcus faecium (1.56 μg/mL). The mechanism of action for this class of compounds appears to be different than clinically used antibiotics. These polyhalogenated benzimidazoles have potential for further investigation as a new class of potent anti‐methicillin‐resistant Staphylococcus aureus and anti‐vancomycin‐resistant Enterococcus faecium agents.

  DOI：

  10.1111/cbdd.12623

文献信息

• Synthesis and<i>In Vitro</i>Activity of Polyhalogenated 2-phenylbenzimidazoles as a New Class of anti-MRSA and Anti-VRE Agents
  作者：Hakan Göker、Cigdem Karaaslan、Mustafa Orhan Püsküllü、Sulhiye Yildiz、Yalcin Duydu、Aylin Üstündağ、Can Özgür Yalcin

  DOI：10.1111/cbdd.12623

  日期：2016.1

  A series of novel polyhalogenated 2‐phenylbenzimidazoles have been synthesized and evaluated for in vitro antistaphylococcal activity against drug‐resistant bacterial strains (methicillin‐resistant Staphylococcus aureus, and vancomycin‐resistant Enterococcus faecium. Certain compounds inhibit bacterial growth perfectly. 11 was active than vancomycin (0.78 μg/mL) with the lowest MIC values with 0.19 μg/mL against methicillin‐resistant Staphylococcus aureus, 8 and 35 exhibited best inhibitory activity against vancomycin‐resistant Enterococcus faecium (1.56 μg/mL). The mechanism of action for this class of compounds appears to be different than clinically used antibiotics. These polyhalogenated benzimidazoles have potential for further investigation as a new class of potent anti‐methicillin‐resistant Staphylococcus aureus and anti‐vancomycin‐resistant Enterococcus faecium agents.