1-[1-(N,N-diethylamino)diazen-1-ium-1,2-diol-2-ato]-2,4-dinitro-5-{[4-(N,N-diethyl-aminocarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diol-2-ato}benzene | 1093077-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-[1-(N,N-diethylamino)diazen-1-ium-1,2-diol-2-ato]-2,4-dinitro-5-{[4-(N,N-diethyl-aminocarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diol-2-ato}benzene
• 英文别名: diethylamino-[5-[[[4-(diethylcarbamoyl)piperazin-1-yl]-oxidoazaniumylidene]amino]oxy-2,4-dinitrophenoxy]imino-oxidoazanium
• CAS: 1093077-94-1
• 化学式: C₁₉H₃₀N₁₀O₉
• 分子量: 542.509
• InChiKey: SZCOGAYBSOXAQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  211.63
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  O2-(2,4-dinitro-5-fluorophenyl) 1-(N,N-diethylamino)diazen-1-ium-1,2-diolate 、 sodium 1-(4-N,N-diethylcarbamoylpiperazin-1-yl)diazen-1-ium-1,2-diolate 以 丙酮 为溶剂， 以90%的产率得到1-[1-(N,N-diethylamino)diazen-1-ium-1,2-diol-2-ato]-2,4-dinitro-5-{[4-(N,N-diethyl-aminocarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diol-2-ato}benzene
  参考文献：
  名称：

  Aryl Bis(diazeniumdiolates): Potent Inducers of S-Glutathionylation of Cellular Proteins and Their in Vitro Antiproliferative Activities

  摘要：

  A number of bis(diazeniumdiolates) that we designed to release up to 4 mol of nitric oxide (NO) and that are structural analogues of the NO prodrug and anticancer lead compound O-2-{2,4-dinitro-5-[4-(N-methylamino)benzoyloxy]phenyl} 1-(N,N-dimethylamino)diazen-1-ium-1,2-diolate (PABA/NO) were synthesized and studied. A majority of these compounds yielded higher levels of NO, were better inhibitors of proliferation of a number of cancer cell lines, and more rapidly induced substantially increased levels of S-glutathionylation of cellular proteins in comparison with PABA/NO. In most cases, the antiproliferative activity and extents of S-glutathionylation correlated well with levels of intracellular NO release. We report bis(diazeniumdiolates) to be a class of S-glutathionylating agents with potent antiproliferative and S-glutathionylating activity.

  DOI：

  10.1021/jm800831y