5-iodo-4-niroimidazole-1-N-(3-picolyl)acetamide N-oxide | 96258-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-iodo-4-niroimidazole-1-N-(3-picolyl)acetamide N-oxide
• 英文别名: 2-(5-iodo-4-nitroimidazol-1-yl)-N-[(1-oxidopyridin-1-ium-3-yl)methyl]acetamide
• CAS: 96258-84-3
• 化学式: C₁₁H₁₀IN₅O₄
• 分子量: 403.136
• InChiKey: ARWYGTPJJBEGKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Imidazole-1-acetic acid, 5-iodo-4-nitro-, ethyl 在 磷酸三乙酯 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 5-iodo-4-niroimidazole-1-N-(3-picolyl)acetamide N-oxide
  参考文献：
  名称：

  Potential radiosensitizing agents. 7. 4(5)-Iodo-5(4)-nitroimidazole derivatives

  摘要：

  A series of 4(5)-iodo-5(4)-nitro-1-substituted-imidazoles has been synthesized and tested for their ability to selectively radiosensitize hypoxic Chinese hamster cells (V-79) to the lethal effect of radiation. The reaction of 4(5)-iodo-5-(4)-nitroimidazole with 1,2-epoxy-3-methoxypropane and ethyl alpha-chloroacetate produced two isomeric products in each case, which were identified by their NMR spectra. The ethyl esters were further reacted with 3-picolylamine to produce corresponding amides. The 5-iodo-4-nitroimidazole-1-N-(3-picolyl)acetamide on further reaction with m-chloroperbenzoic acid produced the corresponding N-oxide. These compounds were generally more toxic to V-79 cells than the 2-nitroimidazole derivatives and were found to be more effective radiosensitizers in vitro. The 5-iodo-4-nitroimidazole derivatives were more efficient as sensitizers than the 4-iodo-5-nitroimidazole derivatives, and the sensitizing efficiency of this class of agents was found to have significant correlation with their partition coefficients.

  DOI：

  10.1021/jm00146a003

文献信息

• GUPTA, RAJENDER, P.;LARROQUETTE, C. A.;AGRAWAL, KRISHNA, C.;GRODKOWSKI, J+, J. MED. CHEM., 1985, 28, N 8, 987-991
  作者：GUPTA, RAJENDER, P.、LARROQUETTE, C. A.、AGRAWAL, KRISHNA, C.、GRODKOWSKI, J+

  DOI：——

  日期：——
• Potential radiosensitizing agents. 7. 4(5)-Iodo-5(4)-nitroimidazole derivatives
  作者：Rajender P. Gupta、Cynthia A. Larroquette、Krishna C. Agrawal、J. Grodkowski、P. Neta

  DOI：10.1021/jm00146a003

  日期：1985.8

  A series of 4(5)-iodo-5(4)-nitro-1-substituted-imidazoles has been synthesized and tested for their ability to selectively radiosensitize hypoxic Chinese hamster cells (V-79) to the lethal effect of radiation. The reaction of 4(5)-iodo-5-(4)-nitroimidazole with 1,2-epoxy-3-methoxypropane and ethyl alpha-chloroacetate produced two isomeric products in each case, which were identified by their NMR spectra. The ethyl esters were further reacted with 3-picolylamine to produce corresponding amides. The 5-iodo-4-nitroimidazole-1-N-(3-picolyl)acetamide on further reaction with m-chloroperbenzoic acid produced the corresponding N-oxide. These compounds were generally more toxic to V-79 cells than the 2-nitroimidazole derivatives and were found to be more effective radiosensitizers in vitro. The 5-iodo-4-nitroimidazole derivatives were more efficient as sensitizers than the 4-iodo-5-nitroimidazole derivatives, and the sensitizing efficiency of this class of agents was found to have significant correlation with their partition coefficients.