1-(2,4-difluorophenyl)-2-(2-methoxy-4-nitro-1H-imidazol-1-yl)ethanol | 1283135-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2,4-difluorophenyl)-2-(2-methoxy-4-nitro-1H-imidazol-1-yl)ethanol
• 英文别名: 1-(2,4-Difluorophenyl)-2-(2-methoxy-4-nitro-imidazol-1-yl)ethanol；1-(2,4-difluorophenyl)-2-(2-methoxy-4-nitroimidazol-1-yl)ethanol
• CAS: 1283135-47-6
• 化学式: C₁₂H₁₁F₂N₃O₄
• 分子量: 299.234
• InChiKey: JHKWGHGFRUQYLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2,4-difluorophenyl)-2-(2-methoxy-4-nitro-1H-imidazol-1-yl)ethanol 、 4-氯苄溴 在 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.5h， 以35%的产率得到1-(2-(4-chlorobenzyloxy)-2-(2,4-difluorophenyl)ethyl)-2-methoxy-4-nitro-1H-imidazole
  参考文献：
  名称：

  Synthesis and antitubercular activity of monocyclic nitroimidazoles: Insights from econazole

  摘要：

  We have designed and synthesized econazole-derived nitroimidazoles to investigate the antitubercular activity of the nitroimidazole compounds. The introduction of a nitro group at the 4-position of the imidazole on econazole abolished the antitubercular activity. However, alcoholic nitroimidazoles 4 and 6 compounds were active against Mycobacterium tuberculosis (Mtb). While the MIC value of econazole was 16 mu g/mL, the MIC of 6a and 6f turned out to be 0.5 mu g/mL. In particular, the activity of 6f against non-replicating Mtb was as good as PA-824, which is currently in clinical phase II studies as an antitubercular agent. Overall, alcohol compounds 4 and 6 tend to be more active than ether compounds 5 and 7. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.128
• 作为产物：
  描述：

  2-chloro-1-(2’,4’-difluorophenyl)ethanol 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 1-(2,4-difluorophenyl)-2-(2-methoxy-4-nitro-1H-imidazol-1-yl)ethanol
  参考文献：
  名称：

  Synthesis and antitubercular activity of monocyclic nitroimidazoles: Insights from econazole

  摘要：

  We have designed and synthesized econazole-derived nitroimidazoles to investigate the antitubercular activity of the nitroimidazole compounds. The introduction of a nitro group at the 4-position of the imidazole on econazole abolished the antitubercular activity. However, alcoholic nitroimidazoles 4 and 6 compounds were active against Mycobacterium tuberculosis (Mtb). While the MIC value of econazole was 16 mu g/mL, the MIC of 6a and 6f turned out to be 0.5 mu g/mL. In particular, the activity of 6f against non-replicating Mtb was as good as PA-824, which is currently in clinical phase II studies as an antitubercular agent. Overall, alcohol compounds 4 and 6 tend to be more active than ether compounds 5 and 7. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.128