1-(4-甲基-2-硝基-1H-咪唑-5-基)乙酮 | 84123-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(4-甲基-2-硝基-1H-咪唑-5-基)乙酮
• 英文名称: 4(5)-acetyl-5(4)-methyl-2-nitroimidazole
• 英文别名: 1-(5-methyl-2-nitro-1H-imidazol-4-yl)ethanone
• CAS: 84123-04-6
• 化学式: C₆H₇N₃O₃
• 分子量: 169.14
• InChiKey: GHUALMJETKJFFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-甲基-2-硝基-1H-咪唑-5-基)乙酮 、 methyloxirane 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 60.0h， 以55%的产率得到4-Acetyl-alpha,5-dimethyl-2-nitroimidazoleethanol
  参考文献：
  名称：

  Potential Radiosensitizing Agents III: 2-Nitro-4-Acetylimidazole Analogs

  摘要：

  New analogs of 2-nitroimidazole have been synthesized in an effort to minimize the toxicity and increase selective sensitization of hypoxic mammalian cells toward lethal effects of ionizing radiation. 2-Nitro-4(5)-acetyl-5(4)-methylimidazole was synthesized from the corresponding 2-amino analog and then reacted with oxiranes to produce the corresponding 1-substituted 2-propanol and 3-methoxy-2-propanol derivatives. The biological results of radiosensitizing activity of these agents against Chinese hamster cells (V-79) indicated that the 3-methoxy-2-propanol derivative was a more effective radiosensitizer than misonidazole in vitro. Evaluation of the acute toxicity of these agents as determined by LD50 demonstrated no significant difference between these agents and misonidazole suggesting that the 3-methoxy-2-propanol analog may possess a therapeutic advantage over misonidazole.

  DOI：

  10.1002/jps.2600711105
• 作为产物：
  描述：

  4(5)-acetyl-5(4)-methyl-2-aminoimidazole 在 tetrafluoroboric acid 、 copper(I) sulfate 、 硫酸 、 sodium nitrite 作用下， 生成 1-(4-甲基-2-硝基-1H-咪唑-5-基)乙酮
  参考文献：
  名称：

  Potential Radiosensitizing Agents III: 2-Nitro-4-Acetylimidazole Analogs

  摘要：

  New analogs of 2-nitroimidazole have been synthesized in an effort to minimize the toxicity and increase selective sensitization of hypoxic mammalian cells toward lethal effects of ionizing radiation. 2-Nitro-4(5)-acetyl-5(4)-methylimidazole was synthesized from the corresponding 2-amino analog and then reacted with oxiranes to produce the corresponding 1-substituted 2-propanol and 3-methoxy-2-propanol derivatives. The biological results of radiosensitizing activity of these agents against Chinese hamster cells (V-79) indicated that the 3-methoxy-2-propanol derivative was a more effective radiosensitizer than misonidazole in vitro. Evaluation of the acute toxicity of these agents as determined by LD50 demonstrated no significant difference between these agents and misonidazole suggesting that the 3-methoxy-2-propanol analog may possess a therapeutic advantage over misonidazole.

  DOI：

  10.1002/jps.2600711105

文献信息

• Sehgal, Raj K., Journal fur praktische Chemie (Leipzig 1954), 1991, vol. 333, # 4, p. 665 - 668
  作者：Sehgal, Raj K.

  DOI：——

  日期：——
• SEHGAL, RAJ, K.;AGRAWAL, KRISHNA, C., J. PHARM. SCI., 1982, 71, N 11, 1203-1206
  作者：SEHGAL, RAJ, K.、AGRAWAL, KRISHNA, C.

  DOI：——

  日期：——