1-(2-hydroxy-3-methoxypropyl)-2,4-dinitroimidazole | 73332-74-8

• 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-hydroxy-3-methoxypropyl)-2,4-dinitroimidazole
• 英文别名: 1-(2,4-dinitro-imidazol-1-yl)-3-methoxy-propan-2-ol；1-(2,4-dinitroimidazol-1-yl)-3-methoxypropan-2-ol
• CAS: 73332-74-8
• 化学式: C₇H₁₀N₄O₆
• 分子量: 246.18
• InChiKey: LNFJOBOCHMMLNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-3-methoxypropyl)-2,4-dinitroimidazole 在 (甲氧基甲基)环氧乙烷 作用下， 以 乙醇 为溶剂， 生成 2-methoxymethyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole
  参考文献：
  名称：

  Sehgal,R.K.; Agrawal,K.C., Journal of Heterocyclic Chemistry, 1979, vol. 16, p. 1499 - 1500

  摘要：

  DOI：
• 作为产物：
  描述：

  (甲氧基甲基)环氧乙烷 、 2,4-二硝基咪唑 以 乙醇 为溶剂， 反应 48.0h， 以48%的产率得到1-(2-hydroxy-3-methoxypropyl)-2,4-dinitroimidazole
  参考文献：
  名称：

  Potential radiosensitizing agents. 2. Synthesis and biological activity of derivatives of dinitroimidazole with oxiranes

  摘要：

  A series of 1-substituted 2,4-dinitroimidazole analogues have been synthesized and tested for their radiosensitizing ability for selectively sensitizing hypoxic mammalian cells to the lethal effect of radiation. The reaction of 2,4-(5)-dinitroimidazole (1) with a variety of oxiranes upon heating in absolute ethanol yielded the expected 1-substituted 2,4-dinitroimidazoles (2) and also resulted in the formation of a novel class of isomeric nitroimidazo[2,1-b]oxazoles 3 and 4) by intramolecular cyclization. The results of radiosensitizing activity of these agents against hypoxic Chinese hamster cells (V-79) indicated that 2,4-dinitroimidazoles were better sensitizers than the nitroimidazo[2,1-b]oxazoles, suggesting the necessity of the 2-nitro function in the molecule. The 1-(2-hydroxy-3-methoxypropyl)-2,4-dinitroimidazole (2d) was found to be the most effective radiosensitizer of this series.

  DOI：

  10.1021/jm00137a021

文献信息

• SEHGAL, R. K.;WEBB, M. W.;AGRAWAL, KRISHNA, C., J. MED. CHEM., 1981, 24, N 5, 601-604
  作者：SEHGAL, R. K.、WEBB, M. W.、AGRAWAL, KRISHNA, C.

  DOI：——

  日期：——
• Sehgal,R.K.; Agrawal,K.C., Journal of Heterocyclic Chemistry, 1979, vol. 16, p. 1499 - 1500
  作者：Sehgal,R.K.、Agrawal,K.C.

  DOI：——

  日期：——
• Potential radiosensitizing agents. 2. Synthesis and biological activity of derivatives of dinitroimidazole with oxiranes
  作者：Raj K. Sehgal、Matthew W. Webb、Krishna C. Agrawal

  DOI：10.1021/jm00137a021

  日期：1981.5

  A series of 1-substituted 2,4-dinitroimidazole analogues have been synthesized and tested for their radiosensitizing ability for selectively sensitizing hypoxic mammalian cells to the lethal effect of radiation. The reaction of 2,4-(5)-dinitroimidazole (1) with a variety of oxiranes upon heating in absolute ethanol yielded the expected 1-substituted 2,4-dinitroimidazoles (2) and also resulted in the formation of a novel class of isomeric nitroimidazo[2,1-b]oxazoles 3 and 4) by intramolecular cyclization. The results of radiosensitizing activity of these agents against hypoxic Chinese hamster cells (V-79) indicated that 2,4-dinitroimidazoles were better sensitizers than the nitroimidazo[2,1-b]oxazoles, suggesting the necessity of the 2-nitro function in the molecule. The 1-(2-hydroxy-3-methoxypropyl)-2,4-dinitroimidazole (2d) was found to be the most effective radiosensitizer of this series.