6-hydroxy-1,2,3,4,5-pentamethoxyacridin-9-one | 135082-44-9

• 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-hydroxy-1,2,3,4,5-pentamethoxyacridin-9-one
• 英文别名: 6-hydroxy-1,2,3,4,5-pentamethoxy-10H-acridin-9-one
• CAS: 135082-44-9
• 化学式: C₁₈H₁₉NO₇
• 分子量: 361.351
• InChiKey: XBSCCHNORVVYOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-hydroxy-1,2,3,4,5-pentamethoxyacridin-9-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以38%的产率得到1,6-dihydroxy-2,3,4,5-tetramethoxy-9-acridone
  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-(苄氧基)-3-甲氧基-2-硝基苯甲酸 在 sodium dithionite 、 PPA 、 铜 、 potassium carbonate 、 copper(II) oxide 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 6.5h， 生成 6-hydroxy-1,2,3,4,5-pentamethoxyacridin-9-one
  参考文献：
  名称：

  甘氨酸的合成，甘氨酸是枸杞子的成分（Willd。）Lindl。和潜在的抗癌药

  摘要：

  4-苄氧基-3- methoxyanthranilic酸（缩合3）与5-碘-1,2,3,4-四甲氧基苯（4），得到6-苄氧基1,2,3,4,5-五甲氧基-9-吖啶酮（5），其随后通过N-甲基化，选择性脱-O-甲基化和脱苄基作用转化为乙二醛（1）。合成的草甘膦（1）与从植物中分离出的真实样品完全相同。

  DOI：

  10.1016/s0040-4039(00)74267-5