10-chloro-5-nitro-1,9-diazaanthracene | 157465-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 10-chloro-5-nitro-1,9-diazaanthracene
• 英文别名: 5-Chloro-6-nitrobenzo[b][1,8]naphthyridine；5-chloro-6-nitrobenzo[b][1,8]naphthyridine
• CAS: 157465-85-5
• 化学式: C₁₂H₆ClN₃O₂
• 分子量: 259.652
• InChiKey: NKFSEBDJWXSSTI-UHFFFAOYSA-N

物化性质

• 沸点：
  469.2±30.0 °C(Predicted)
• 密度：
  1.546±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  C.I.酸性橙108 、 10-chloro-5-nitro-1,9-diazaanthracene 在 苯酚 作用下， 生成 10-(2-hydroxyethylamino)-5-nitro-1,9-diazaanthracene
  参考文献：
  名称：

  Hypoxia-selective antitumor agents derived from 1,9-diazaanthracene

  摘要：

  The nitroacridine derivative 9-[3-(N,N-dimethylamino)propylamino]-1-nitroacridine (nitracrine) is a potent hypoxia-selective cytotoxin for tumor cells in culture. Modifications of the acridine ring result in altered DNA binding properties. This has suggested the possibility of preparing new nitracrine analogues retaining the nitro group and the alkylamino lateral chain. In this paper we describe the synthesis of the new diazaanthracenes 4, 5, 6 in order to study the relationships between the heterocyclic system and the hypoxia-selective cytotoxicity. This class of new bioreductive agents may constitute a group of potential interest for the design of new cytotoxins.

  DOI：

  10.1016/0223-5234(94)90071-x
• 作为产物：
  描述：

  间硝基苯胺 在 铜 、 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 10-chloro-5-nitro-1,9-diazaanthracene
  参考文献：
  名称：

  Hypoxia-selective antitumor agents derived from 1,9-diazaanthracene

  摘要：

  The nitroacridine derivative 9-[3-(N,N-dimethylamino)propylamino]-1-nitroacridine (nitracrine) is a potent hypoxia-selective cytotoxin for tumor cells in culture. Modifications of the acridine ring result in altered DNA binding properties. This has suggested the possibility of preparing new nitracrine analogues retaining the nitro group and the alkylamino lateral chain. In this paper we describe the synthesis of the new diazaanthracenes 4, 5, 6 in order to study the relationships between the heterocyclic system and the hypoxia-selective cytotoxicity. This class of new bioreductive agents may constitute a group of potential interest for the design of new cytotoxins.

  DOI：

  10.1016/0223-5234(94)90071-x