1-hydroxy-7-nitro-4-(7-nitro-1,2,3-trimethoxyacridin-9-yl)-2,3-dimethoxyacridin-9-one | 142003-97-2

• 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: 1-hydroxy-7-nitro-4-(7-nitro-1,2,3-trimethoxyacridin-9-yl)-2,3-dimethoxyacridin-9-one
• CAS: 142003-97-2
• 化学式: C₃₁H₂₄N₄O₁₁
• 分子量: 628.552
• InChiKey: JULQXOMKIRBYRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  198.41
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯胺 在 copper(I) oxide 、 PPA 、 铜 、 potassium carbonate 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 6.0h， 生成 1-hydroxy-7-nitro-4-(7-nitro-1,2,3-trimethoxyacridin-9-yl)-2,3-dimethoxyacridin-9-one
  参考文献：
  名称：

  Synthesis of the acridone alkaloids, glyfoline and congeners. Structure-activity relationship studies of cytotoxic acridones

  摘要：

  Glyfoline (4, 1,6-dihydroxY-10-methyl-2,3,4,5-tetramethoxyacridin-9-one) and its congeners were synthesized for evaluation of their cytotoxicity. A detailed structure-activity relationships (SAR) of these acridone derivatives were also studied. To study the SAR of glyfoline analogues, substituent(s) at C-1 and C-6 and at the heterocyclic nitrogen of glyfoline nucleus were modified. Nitro- and amino-substituted glyfoline analogues were also synthesized to study the effects of substituent(s) (electron-withdrawing vs electron-donating) on their cytotoxicity. These compounds were synthesized via the Ullmann condensation of anthranilic acids with iodobenzenes or 2-chlorobenzoic acids with aniline-derivatives. The SAR studies showed that 1-hydroxy 9-acridones were more active than their 1-OMe derivatives against cell growth of human leukemic HL-60 cells in culture. Replacement of NMe of glyfoline with NH or N(CH2)2NEt2 resulted in either total loss or dramatic reduction of cytotoxity. Glyfoline congeners with nitro function at the A-ring were inactive, while compounds with amino substituent were shown to be cytotoxic in vitro.

  DOI：

  10.1021/jm00092a022