3,9-dinitro-acenaphtho[1,2-b]quinoxaline | 1021397-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,9-dinitro-acenaphtho[1,2-b]quinoxaline
• 英文别名: 3,9-Dinitroacenaphthyleno[1,2-b]quinoxaline
• CAS: 1021397-13-6
• 化学式: C₁₈H₈N₄O₄
• 分子量: 344.286
• InChiKey: VLKXFRYSMZJSAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,9-dinitro-acenaphtho[1,2-b]quinoxaline 在 盐酸 、 tin(ll) chloride 作用下， 反应 4.0h， 以40%的产率得到acenaphtho[1,2-b]quinoxaline-3,9-diamine
  参考文献：
  名称：

  Novel nitroheterocyclic hypoxic markers for solid tumor: Synthesis and biological evaluation

  摘要：

  Based on the principle that the nitro-group can quench the fluorescence and can be reduced under hypoxic conditions, several novel nitroheterocyclic compounds without 2-nitroimidazole as potential hypoxic markers were prepared. Although they were synthesized from the same matrix, nitrosubstituted acenaphtho[1,2-b]quinoxaline, these compounds exhibited quite different fluorescence changes when they were differently nitrosubstituted. Their evaluation for imaging tumor hypoxia was carried out in V79 cells in vitro by Fluorescence Microplate Reader. After 3.5 h, the hypoxic-oxic fluorescence differential incubated with A1, A4, and A5 in V79 cells could reach 6, 9, and 11 times differential fluorescence between oxic and hypoxic cells separately, which are suitable for further evaluation as probes for hypoxic cells in tumors in vivo. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.011
• 作为产物：
  描述：

  5-nitro-acenaphthylene-1,2-dione 、 4-硝基邻苯二胺 以 溶剂黄146 为溶剂， 反应 1.0h， 以80%的产率得到3,9-dinitro-acenaphtho[1,2-b]quinoxaline
  参考文献：
  名称：

  Novel nitroheterocyclic hypoxic markers for solid tumor: Synthesis and biological evaluation

  摘要：

  Based on the principle that the nitro-group can quench the fluorescence and can be reduced under hypoxic conditions, several novel nitroheterocyclic compounds without 2-nitroimidazole as potential hypoxic markers were prepared. Although they were synthesized from the same matrix, nitrosubstituted acenaphtho[1,2-b]quinoxaline, these compounds exhibited quite different fluorescence changes when they were differently nitrosubstituted. Their evaluation for imaging tumor hypoxia was carried out in V79 cells in vitro by Fluorescence Microplate Reader. After 3.5 h, the hypoxic-oxic fluorescence differential incubated with A1, A4, and A5 in V79 cells could reach 6, 9, and 11 times differential fluorescence between oxic and hypoxic cells separately, which are suitable for further evaluation as probes for hypoxic cells in tumors in vivo. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.011

文献信息

• Novel nitroheterocyclic hypoxic markers for solid tumor: Synthesis and biological evaluation
  作者：Weiping Zhu、Min Dai、Yufang Xu、Xuhong Qian

  DOI：10.1016/j.bmc.2007.12.011

  日期：2008.3.15

  Based on the principle that the nitro-group can quench the fluorescence and can be reduced under hypoxic conditions, several novel nitroheterocyclic compounds without 2-nitroimidazole as potential hypoxic markers were prepared. Although they were synthesized from the same matrix, nitrosubstituted acenaphtho[1,2-b]quinoxaline, these compounds exhibited quite different fluorescence changes when they were differently nitrosubstituted. Their evaluation for imaging tumor hypoxia was carried out in V79 cells in vitro by Fluorescence Microplate Reader. After 3.5 h, the hypoxic-oxic fluorescence differential incubated with A1, A4, and A5 in V79 cells could reach 6, 9, and 11 times differential fluorescence between oxic and hypoxic cells separately, which are suitable for further evaluation as probes for hypoxic cells in tumors in vivo. (C) 2007 Elsevier Ltd. All rights reserved.