(Z)-[5-(2-acetyloxybenzoyl)oxy-2,4-dinitrophenoxy]imino-(dimethylamino)-oxidoazanium | 1025061-12-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: (Z)-[5-(2-acetyloxybenzoyl)oxy-2,4-dinitrophenoxy]imino-(dimethylamino)-oxidoazanium
• CAS: 1025061-12-4
• 化学式: C₁₇H₁₅N₅O₁₀
• 分子量: 449.334
• InChiKey: MJZFDSMFOCKBRT-PYCFMQQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  198
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  O²-(2,4-dinitro-5-hydroxyphenyl) 1-(N,N-dimethylamino)diazen-1-ium-1,2-diolate 、 邻乙酰水杨酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到(Z)-[5-(2-acetyloxybenzoyl)oxy-2,4-dinitrophenoxy]imino-(dimethylamino)-oxidoazanium
  参考文献：
  名称：

  Synthesis, nitric oxide release, and anti-leukemic activity of glutathione-activated nitric oxide prodrugs: Structural analogues of PABA/NO, an anti-cancer lead compound

  摘要：

  Diazeniumdiolate anions and their prodrug forms are reliable sources of nitric oxide (NO) that have generated interest as promising therapeutic agents. A number of structural analogues of O-2-(2,4-dinitro-5-(4-(N-methylamino)benzoyloxy)phenyl)-1-(N,N-dimetliylamino)diazen-1-ium-1,2-diolate (PABA/NO), an anti-cancer lead compound that is designed to release NO upon activation by glutathione, were prepared. The nitric oxide release patterns of these O-2-(2,4-dinitrophenyl) diazeniumdiolates in the presence of glutathione were tested and it was found that in the absence of competing pathways, these compounds release nearly quantitative amounts of NO. The ability of PABA/NO and its structural analogues to inhibit human leukemia cell proliferation was determined and it was found that compounds releasing elevated amounts of NO displayed superior cytotoxic effects. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.035

文献信息

• Synthesis, nitric oxide release, and anti-leukemic activity of glutathione-activated nitric oxide prodrugs: Structural analogues of PABA/NO, an anti-cancer lead compound
  作者：Harinath Chakrapani、Thomas C. Wilde、Michael L. Citro、Michael M. Goodblatt、Larry K. Keefer、Joseph E. Saavedra

  DOI：10.1016/j.bmc.2007.11.035

  日期：2008.3

  Diazeniumdiolate anions and their prodrug forms are reliable sources of nitric oxide (NO) that have generated interest as promising therapeutic agents. A number of structural analogues of O-2-(2,4-dinitro-5-(4-(N-methylamino)benzoyloxy)phenyl)-1-(N,N-dimetliylamino)diazen-1-ium-1,2-diolate (PABA/NO), an anti-cancer lead compound that is designed to release NO upon activation by glutathione, were prepared. The nitric oxide release patterns of these O-2-(2,4-dinitrophenyl) diazeniumdiolates in the presence of glutathione were tested and it was found that in the absence of competing pathways, these compounds release nearly quantitative amounts of NO. The ability of PABA/NO and its structural analogues to inhibit human leukemia cell proliferation was determined and it was found that compounds releasing elevated amounts of NO displayed superior cytotoxic effects. (C) 2007 Elsevier Ltd. All rights reserved.