Ethyl 2-(2,6-dinitrobenzimidazol-1-yl)acetate | 83167-06-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 2-(2,6-dinitrobenzimidazol-1-yl)acetate
• CAS: 83167-06-0
• 化学式: C₁₁H₁₀N₄O₆
• 分子量: 294.224
• InChiKey: KJGIODYMZURFOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-硝基-1H-苯并咪唑 在 硫酸 、 potassium carbonate 、 potassium nitrate 作用下， 以 乙腈 为溶剂， 反应 7.5h， 生成 Ethyl 2-(2,6-dinitrobenzimidazol-1-yl)acetate
  参考文献：
  名称：

  Potential radiosensitizing agents. 5. 2-Substituted benzimidazole derivatives

  摘要：

  A series of 2-substituted benzimidazoles and their derivatives have been synthesized and tested for their ability to selectively sensitize hypoxic Chinese hamster cells (V-79) toward the lethal effect of ionizing radiation. These compounds were prepared by reacting the 2-substituted benzimidazoles with 1,2-epoxy-3-methoxypropane in the presence of potassium carbonate. Reaction of the 2-nitro and 2-methylfonyl analogue with the epoxide also yielded a cyclized material, which was confirmed to be a benzimidazo[2,1-b]oxazole. In an attempt to increase the electron affinity, 5- or 6-nitro-2-substituted-benzimidazoles were also synthesized and then reacted with the epoxide to yield the corresponding 1-substituted derivatives. The results of the biological tests for the radiosensitizing activity of these agents against Chinese hamster cells (V-79) in culture indicated that the 2-nitro-substituted analogues were the most effective sensitizers in this series.

  DOI：

  10.1021/jm00353a014

文献信息

• GUPTA, R. P.;LARROQUETTE, C. A.;AGRAWAL, K. C., J. MED. CHEM., 1982, 25, N 11, 1342-1346
  作者：GUPTA, R. P.、LARROQUETTE, C. A.、AGRAWAL, K. C.

  DOI：——

  日期：——
• Potential radiosensitizing agents. 5. 2-Substituted benzimidazole derivatives
  作者：Rajender P. Gupta、Cynthia A. Larroquette、Krishna C. Agrawal

  DOI：10.1021/jm00353a014

  日期：1982.11

  A series of 2-substituted benzimidazoles and their derivatives have been synthesized and tested for their ability to selectively sensitize hypoxic Chinese hamster cells (V-79) toward the lethal effect of ionizing radiation. These compounds were prepared by reacting the 2-substituted benzimidazoles with 1,2-epoxy-3-methoxypropane in the presence of potassium carbonate. Reaction of the 2-nitro and 2-methylfonyl analogue with the epoxide also yielded a cyclized material, which was confirmed to be a benzimidazo[2,1-b]oxazole. In an attempt to increase the electron affinity, 5- or 6-nitro-2-substituted-benzimidazoles were also synthesized and then reacted with the epoxide to yield the corresponding 1-substituted derivatives. The results of the biological tests for the radiosensitizing activity of these agents against Chinese hamster cells (V-79) in culture indicated that the 2-nitro-substituted analogues were the most effective sensitizers in this series.