N-(oxiranylmethyl)-5-nitrofuran-2-carboxamide | 143134-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: N-(oxiranylmethyl)-5-nitrofuran-2-carboxamide
• 英文别名: 5-nitro-N-(oxiran-2-ylmethyl)furan-2-carboxamide
• CAS: 143134-32-1
• 化学式: C₈H₈N₂O₅
• 分子量: 212.162
• InChiKey: PVZGXTBHOQSHIK-UHFFFAOYSA-N

物化性质

• 沸点：
  424.4±30.0 °C(Predicted)
• 密度：
  1.465±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(oxiranylmethyl)-5-nitrofuran-2-carboxamide 、 cis-2,3-dimethylaziridine 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以32%的产率得到N-(3-(cis-2,3-dimethyl-1-aziridinyl)-2-hydroxypropyl)-5-nitrofuran-2-carboxamide
  参考文献：
  名称：

  Synthesis and evaluation of novel electrophilic nitrofuran carboxamides and carboxylates as radiosensitizers and bioreductively activated cytotoxins

  摘要：

  A series of 5-nitrofuran-2- and 3-carboxamides bearing alkylating side-chains has been synthesized and tested for their ability to radiosensitize selectively hypoxic Chinese hamster cells (V79) to the lethal effects of ionizing radiation and also for their ability to act directly and selectively as cytotoxic drugs on hypoxic V79 cells. The compounds were extremely efficient radiosensitizers of such cells in vitro and were more efficient than known nitroimidazoles of similar type. Their efficiencies as radiosensitizers correlated with their high electron affinity (E7(1] as measured by pulse-radiolysis. However the compounds showed little radiosensitizing activity towards KHT sarcomas in C3H mice. The compounds in this series of nitrofurans were generally more toxic towards hypoxic cells than towards oxic cells in vitro but were less effective upon the basis of a differential effect than were similar nitroimidazoles reported previously.

  DOI：

  10.1021/jm00171a027
• 作为产物：
  描述：

  5-硝基-2-糠酰氯 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 N-(oxiranylmethyl)-5-nitrofuran-2-carboxamide
  参考文献：
  名称：

  Synthesis and evaluation of novel electrophilic nitrofuran carboxamides and carboxylates as radiosensitizers and bioreductively activated cytotoxins

  摘要：

  A series of 5-nitrofuran-2- and 3-carboxamides bearing alkylating side-chains has been synthesized and tested for their ability to radiosensitize selectively hypoxic Chinese hamster cells (V79) to the lethal effects of ionizing radiation and also for their ability to act directly and selectively as cytotoxic drugs on hypoxic V79 cells. The compounds were extremely efficient radiosensitizers of such cells in vitro and were more efficient than known nitroimidazoles of similar type. Their efficiencies as radiosensitizers correlated with their high electron affinity (E7(1] as measured by pulse-radiolysis. However the compounds showed little radiosensitizing activity towards KHT sarcomas in C3H mice. The compounds in this series of nitrofurans were generally more toxic towards hypoxic cells than towards oxic cells in vitro but were less effective upon the basis of a differential effect than were similar nitroimidazoles reported previously.

  DOI：

  10.1021/jm00171a027

文献信息

• NAYLOR, MATTHEW A.;STEPHENS, MIRIAM A.;COLE, SHIRLEY;THREADGILL, MICHAEL +, J. MED. CHEM., 33,(1990) N, C. 2508-2513
  作者：NAYLOR, MATTHEW A.、STEPHENS, MIRIAM A.、COLE, SHIRLEY、THREADGILL, MICHAEL +

  DOI：——

  日期：——
• Synthesis and evaluation of novel electrophilic nitrofuran carboxamides and carboxylates as radiosensitizers and bioreductively activated cytotoxins
  作者：Matthew A. Naylor、Miriam A. Stephens、Shirley Cole、Michael D. Threadgill、Ian J. Stratford、Peter O'Neill、E. Martin Fielden、Gerald E. Adams

  DOI：10.1021/jm00171a027

  日期：1990.9

  A series of 5-nitrofuran-2- and 3-carboxamides bearing alkylating side-chains has been synthesized and tested for their ability to radiosensitize selectively hypoxic Chinese hamster cells (V79) to the lethal effects of ionizing radiation and also for their ability to act directly and selectively as cytotoxic drugs on hypoxic V79 cells. The compounds were extremely efficient radiosensitizers of such cells in vitro and were more efficient than known nitroimidazoles of similar type. Their efficiencies as radiosensitizers correlated with their high electron affinity (E7(1] as measured by pulse-radiolysis. However the compounds showed little radiosensitizing activity towards KHT sarcomas in C3H mice. The compounds in this series of nitrofurans were generally more toxic towards hypoxic cells than towards oxic cells in vitro but were less effective upon the basis of a differential effect than were similar nitroimidazoles reported previously.