6-Amino-1-hydroxy-2,3,4-trimethoxy-10-methyl-10H-acridin-9-one | 142004-11-3

• 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-Amino-1-hydroxy-2,3,4-trimethoxy-10-methyl-10H-acridin-9-one
• 英文别名: 6-Amino-1-hydroxy-2,3,4-trimethoxy-10-methylacridin-9-one
• CAS: 142004-11-3
• 化学式: C₁₇H₁₈N₂O₅
• 分子量: 330.34
• InChiKey: QBDNDJARULDSCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  94.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-Amino-1-hydroxy-2,3,4-trimethoxy-10-methyl-10H-acridin-9-one 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以20%的产率得到6-Dimethylamino-1-hydroxy-2,3,4-trimethoxy-10-methyl-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 palladium on activated charcoal 盐酸 、 PPA 、 氢气 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 丙酮 为溶剂， 90.0 ℃ 、275.79 kPa 条件下， 反应 31.0h， 生成 6-Amino-1-hydroxy-2,3,4-trimethoxy-10-methyl-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

文献信息

• Synthesis of the acridone alkaloids, glyfoline and congeners. Structure-activity relationship studies of cytotoxic acridones
  作者：Tsann Long Su、Bernd Kohler、Ting Chao Chou、Moon Woo Chun、Kyoichi A. Watanabe

  DOI：10.1021/jm00092a022

  日期：1992.7

  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.