N-[3-(2-Hydroxy-ethyl)-2,6-dimethyl-4-nitro-3H-benzoimidazol-5-yl]-acetamide | 835627-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N-[3-(2-Hydroxy-ethyl)-2,6-dimethyl-4-nitro-3H-benzoimidazol-5-yl]-acetamide
• CAS: 835627-68-4
• 化学式: C₁₃H₁₆N₄O₄
• 分子量: 292.294
• InChiKey: OKXITTROGCWSLK-UHFFFAOYSA-N

物化性质

• 熔点：
  225-230 °C
• 沸点：
  597.0±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  110.29
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[3-(2-Hydroxy-ethyl)-2,6-dimethyl-4-nitro-3H-benzoimidazol-5-yl]-acetamide 在 palladium on activated charcoal 吡啶 、 phosphate buffer 、 potassium nitrososulfonate 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 3.5h， 生成 7-acetamido-2,8-dimethyl-4,5-dihydroimidazo[1,5,4-de]quinoxalin-9-one
  参考文献：
  名称：

  Synthesis of imidazo[1,5,4-de]quinoxalin-9-ones, benzimidazole analogues of pyrroloiminoquinone marine natural products

  摘要：

  The imidazoquinoxalinones 1 and 2 are benzimidazole analogues of indole-based marine natural products called makaluvamins. The stabilized cation 1 and the zwitterion 2 were prepared in similar to9 steps from readily available starting materials. Compound 1 is more cytostatic and cytotoxic than 2 and also shows activity in the hollow fiber assay. Unlike the indole-based natural products, 1 and 2 are not potent topoisomerase II inhibitors. Their pattern of cytotoxic and cyostatic activity could be related to inhibition of protein tyrosine kinases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.016
• 作为产物：
  描述：

  6-乙酰氨基-1-(2-乙酰氧基乙基)-2,3-二甲基-7-硝基苯并咪唑 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以98%的产率得到N-[3-(2-Hydroxy-ethyl)-2,6-dimethyl-4-nitro-3H-benzoimidazol-5-yl]-acetamide
  参考文献：
  名称：

  Synthesis of imidazo[1,5,4-de]quinoxalin-9-ones, benzimidazole analogues of pyrroloiminoquinone marine natural products

  摘要：

  The imidazoquinoxalinones 1 and 2 are benzimidazole analogues of indole-based marine natural products called makaluvamins. The stabilized cation 1 and the zwitterion 2 were prepared in similar to9 steps from readily available starting materials. Compound 1 is more cytostatic and cytotoxic than 2 and also shows activity in the hollow fiber assay. Unlike the indole-based natural products, 1 and 2 are not potent topoisomerase II inhibitors. Their pattern of cytotoxic and cyostatic activity could be related to inhibition of protein tyrosine kinases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.016