6-(benzyloxy)-10-<2-(diethylamino)ethyl>-1,2,3,4,5-pentamethoxyacridin-9-one | 142003-86-9

• 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: 6-(benzyloxy)-10-<2-(diethylamino)ethyl>-1,2,3,4,5-pentamethoxyacridin-9-one
• 英文别名: 10-[2-(diethylamino)ethyl]-1,2,3,4,5-pentamethoxy-6-phenylmethoxyacridin-9-one
• CAS: 142003-86-9
• 化学式: C₃₁H₃₈N₂O₇
• 分子量: 550.652
• InChiKey: MJLDXVZHMLVGBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  40.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  80.62
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  6-(benzyloxy)-10-<2-(diethylamino)ethyl>-1,2,3,4,5-pentamethoxyacridin-9-one 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 10-(2-Diethylamino-ethyl)-1,6-dihydroxy-2,3,4,5-tetramethoxy-10H-acridin-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
• 作为产物：
  描述：

  4-(benzyloxy)-3-methoxy-N-(2,3,4,5-tetramethoxyphenyl)anthranilic acid 在 哌啶 、 吡啶 、 氯化亚砜 、 sodium hydride 、 三乙胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 23.0h， 生成 6-(benzyloxy)-10-<2-(diethylamino)ethyl>-1,2,3,4,5-pentamethoxyacridin-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