1-[1-(N,N-dimethylamino)diazen-1-ium-1,2-diol-2-ato]-2,4-dinitro-5-[(pyrrolidin-1-yl)diazen-1-ium-1,2-diol-2-ato]benzene | 1093077-89-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[1-(N,N-dimethylamino)diazen-1-ium-1,2-diol-2-ato]-2,4-dinitro-5-[(pyrrolidin-1-yl)diazen-1-ium-1,2-diol-2-ato]benzene
• 英文别名: dimethylamino-[2,4-dinitro-5-[[oxido(pyrrolidin-1-yl)azaniumylidene]amino]oxyphenoxy]imino-oxidoazanium
• CAS: 1093077-89-4
• 化学式: C₁₂H₁₆N₈O₈
• 分子量: 400.308
• InChiKey: TUWLBJKEBDSAPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  188.08
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  sodium 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate 、 O²-(2,4-dinitro-5-fluorophenyl) 1-(N,N-dimethylamino)diazen-1-ium-1,2-diolate 以 丙酮 为溶剂， 以79%的产率得到1-[1-(N,N-dimethylamino)diazen-1-ium-1,2-diol-2-ato]-2,4-dinitro-5-[(pyrrolidin-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