1-[1-(N,N-diethylamino)diazen-1-ium-1,2-diol-2-ato]-2,4-dinitro-5-{[(2-hydroxymethyl)-pyrrolidin-1-yl]diazen-1-ium-1,2-diol-2-ato}benzene | 1093077-95-2

• 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-diethylamino)diazen-1-ium-1,2-diol-2-ato]-2,4-dinitro-5-{[(2-hydroxymethyl)-pyrrolidin-1-yl]diazen-1-ium-1,2-diol-2-ato}benzene
• CAS: 1093077-95-2
• 化学式: C₁₅H₂₂N₈O₉
• 分子量: 458.388
• InChiKey: VLNFHXSRGYSBBZ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  208.31
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  (S)-1-[2-(hydroxymethyl)pyrrolidin-1-yl]diazen-1-ium-1,2-diolate sodium salt 、 O2-(2,4-dinitro-5-fluorophenyl) 1-(N,N-diethylamino)diazen-1-ium-1,2-diolate 以 丙酮 为溶剂， 以87%的产率得到1-[1-(N,N-diethylamino)diazen-1-ium-1,2-diol-2-ato]-2,4-dinitro-5-{[(2-hydroxymethyl)-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