2-(2-bromo-4-nitro-1H-imidazol-1-yl)-1-(2,4-difluorophenyl)ethanol | 1283135-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-bromo-4-nitro-1H-imidazol-1-yl)-1-(2,4-difluorophenyl)ethanol
• 英文别名: 2-(2-Bromo-4-nitro-imidazol-1-yl)-1-(2,4-difluorophenyl)ethanol；2-(2-bromo-4-nitroimidazol-1-yl)-1-(2,4-difluorophenyl)ethanol
• CAS: 1283135-22-7
• 化学式: C₁₁H₈BrF₂N₃O₃
• 分子量: 348.104
• InChiKey: ZXSHPNMZGADMJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-bromo-4-nitro-1H-imidazol-1-yl)-1-(2,4-difluorophenyl)ethanol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以60%的产率得到2-(2,4-difluorophenyl)-2,3-dihydro-6-nitro-imidazo[2,1-b]oxazole
  参考文献：
  名称：

  바이시클릭니트로이미다졸 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 결핵의 예방 또는 치료용 약학적 조성물

  摘要：

  本发明涉及一种双环氮咪唑衍生物或其药学上可接受的盐，其制备方法以及含有其作为有效成分的结核病预防或治疗用药学组合物，根据本发明，新型双环氮咪唑衍生物对结核杆菌在各种环境中表现出优异的抗结核功效，因此可用作结核病的预防或治疗用药学组合物。

  公开号：

  KR101650716B1
• 作为产物：
  描述：

  2-chloro-1-(2’,4’-difluorophenyl)ethanol 、 2-溴-4-硝基咪唑 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 以24%的产率得到2-(2-bromo-4-nitro-1H-imidazol-1-yl)-1-(2,4-difluorophenyl)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

文献信息

• 바이시클릭니트로이미다졸 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 결핵의 예방 또는 치료용 약학적 조성물
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY 한국화학연구원(319980077651)

  公开号：KR101650716B1

  公开（公告）日：2016-08-24

  본 발명은 바이시클릭니트로이미다졸 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 결핵의 예방 또는 치료용 약학적 조성물에 관한 것으로, 본 발명에 따른 신규한 바이시클릭니트로이미다졸 유도체는 다양한 환경에서의 결핵균에 대하여 우수한 항결핵 효능을 나타내므로, 결핵의 예방 또는 치료용 약학적 조성물로 유용할 수 있다.

  本发明涉及一种双环氮咪唑衍生物或其药学上可接受的盐，其制备方法以及含有其作为有效成分的结核病预防或治疗用药学组合物，根据本发明，新型双环氮咪唑衍生物对结核杆菌在各种环境中表现出优异的抗结核功效，因此可用作结核病的预防或治疗用药学组合物。
• Synthesis and antitubercular activity of monocyclic nitroimidazoles: Insights from econazole
  作者：Sang-Ho Lee、Suhyun Kim、Min-Han Yun、Yong Sup Lee、Sang-Nae Cho、Taegwon Oh、Pilho Kim

  DOI：10.1016/j.bmcl.2010.12.128

  日期：2011.3

  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.