2-(4-氟苯基)-1,4-二甲基-5-硝基咪唑 | 104575-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(4-氟苯基)-1,4-二甲基-5-硝基咪唑
• 中文别名: 1-哌啶羧酸,2-[[[4-(三氟甲基)苯基]氨基]甲基]-,1,1-二甲基乙基酯
• 英文名称: 1,4-dimethyl-2-(4-fluorophenyl)-5-nitroimidazole
• 英文别名: 1H-Imidazole, 2-(4-fluorophenyl)-1,4-dimethyl-5-nitro-；2-(4-fluorophenyl)-1,4-dimethyl-5-nitroimidazole
• CAS: 104575-25-9
• 化学式: C₁₁H₁₀FN₃O₂
• 分子量: 235.218
• InChiKey: RPGSCNXOVOIKNC-UHFFFAOYSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  395.5±52.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 2-(4-氟苯基)-1,4-二甲基-5-硝基咪唑 以 水 、 二甲基亚砜 为溶剂， 反应 40.0h， 以7.5%的产率得到2-[2-(4-氟苯基)-1-甲基-5-硝基咪唑-4-基]乙醇
  参考文献：
  名称：

  Structural alterations that differentially affect the mutagenic and antitrichomonal activities of 5-nitroimidazoles

  摘要：

  Two approaches have been used to develop nonmutagenic 5-nitroimidazoles. Both approaches are based on knowledge of the likely mechanisms by which this class of compounds cause mutagenicity. The first approach involved incorporating readily oxidizable gallate derivatives into the molecule. In one case, a very weakly mutagenic active antitrichomonal agent was obtained. The second approach involved incorporating a substituent at the C4 position of the ring. This generally resulted in a large reduction in mutagenicity and a lowering of antitrichomonal activity in vitro. In certain cases, however, mutagenicity was dramatically reduced while moderate antitrichomonal activity was retained. For example, 1,2-dimethyl-4-(2-hydroxyethyl)-5-nitroimidazole (5) showed good antitrichomonal activity in vitro (ED50 = 2 micrograms/kg) while possessing only 4% of the mutagenicity of metronidazole.

  DOI：

  10.1021/jm00384a025
• 作为产物：
  描述：

  2-(4-氟苯基)-4-甲基-1H-咪唑 在 硝酸 、 乙酸酐 作用下， 以 乙二醇二甲醚 、 乙醚 为溶剂， 反应 1.25h， 生成 2-(4-氟苯基)-1,4-二甲基-5-硝基咪唑
  参考文献：
  名称：

  Structural alterations that differentially affect the mutagenic and antitrichomonal activities of 5-nitroimidazoles

  摘要：

  Two approaches have been used to develop nonmutagenic 5-nitroimidazoles. Both approaches are based on knowledge of the likely mechanisms by which this class of compounds cause mutagenicity. The first approach involved incorporating readily oxidizable gallate derivatives into the molecule. In one case, a very weakly mutagenic active antitrichomonal agent was obtained. The second approach involved incorporating a substituent at the C4 position of the ring. This generally resulted in a large reduction in mutagenicity and a lowering of antitrichomonal activity in vitro. In certain cases, however, mutagenicity was dramatically reduced while moderate antitrichomonal activity was retained. For example, 1,2-dimethyl-4-(2-hydroxyethyl)-5-nitroimidazole (5) showed good antitrichomonal activity in vitro (ED50 = 2 micrograms/kg) while possessing only 4% of the mutagenicity of metronidazole.

  DOI：

  10.1021/jm00384a025

文献信息

• WALSH J. S.; WANG R.; BAGAN E.; WANG C. C.; WISLOCKI P.; MIWA G. T., J. MED. CHEM., 30,(1987) N 1, 150-156
  作者：WALSH J. S.、 WANG R.、 BAGAN E.、 WANG C. C.、 WISLOCKI P.、 MIWA G. T.

  DOI：——

  日期：——
• Structural alterations that differentially affect the mutagenic and antitrichomonal activities of 5-nitroimidazoles
  作者：John S. Walsh、Regina Wang、Edward Bagan、C. C. Wang、Peter Wislocki、Gerald T. Miwa

  DOI：10.1021/jm00384a025

  日期：1987.1

  Two approaches have been used to develop nonmutagenic 5-nitroimidazoles. Both approaches are based on knowledge of the likely mechanisms by which this class of compounds cause mutagenicity. The first approach involved incorporating readily oxidizable gallate derivatives into the molecule. In one case, a very weakly mutagenic active antitrichomonal agent was obtained. The second approach involved incorporating a substituent at the C4 position of the ring. This generally resulted in a large reduction in mutagenicity and a lowering of antitrichomonal activity in vitro. In certain cases, however, mutagenicity was dramatically reduced while moderate antitrichomonal activity was retained. For example, 1,2-dimethyl-4-(2-hydroxyethyl)-5-nitroimidazole (5) showed good antitrichomonal activity in vitro (ED50 = 2 micrograms/kg) while possessing only 4% of the mutagenicity of metronidazole.