3-acetoxy-1-hydroxy-2-methylanthraquinone | 10383-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-acetoxy-1-hydroxy-2-methylanthraquinone
• 英文别名: Rubiadin-3-acetat；3-Acetoxy-1-hydroxy-2-methyl-anthrachinon；(4-Hydroxy-3-methyl-9,10-dioxoanthracen-2-yl) acetate；(4-hydroxy-3-methyl-9,10-dioxoanthracen-2-yl) acetate
• CAS: 10383-64-9
• 化学式: C₁₇H₁₂O₅
• 分子量: 296.279
• InChiKey: PNCWOXZFWLCBNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetoxy-1-hydroxy-2-methylanthraquinone 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 sodium hydroxide 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 水 、 丙酮 为溶剂， 反应 118.0h， 生成 4-bromo-2-formyl-3-hydroxy-1-methoxyanthraquinone
  参考文献：
  名称：

  Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines

  摘要：

  Damnacanthal and nordamnacanthal, two naturally occurring 9,10-anthraquinones, and their analogues were synthesized. Cytotoxic activity against five cancer cell lines was evaluated using MTT assay. 2-Bromomethyl-1,3-dimethoxyanthraquinone was found to display the highest activity against all cell lines with IC50 range of 2-8 mu M. Structure-activity relationship (SAR) assessment was considered to rationalise the cytotoxic effect. Bromomethyl group at position C-2 of the anthraquinone was found to be important in exerting cytotoxic activity of this class of compounds. The presence of the flanking methoxyl or hydroxyl groups at C-1 and C-3 also contributes to this activity. Finally, the antioxidant effect of these compounds was evaluated. MTT assay was used to measure the cytotoxicity against different cancer cell lines. Antioxidant activity was measured by FTC and TBA methods. Only two anthraquinones, damnacanthal and nordamnacanthal, were found to be antioxidative.

  DOI：

  10.1007/s00044-012-0197-5
• 作为产物：
  描述：

  2,6-二羟基甲苯 在 aluminum (III) chloride 、 potassium carbonate 、 sodium chloride 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 3-acetoxy-1-hydroxy-2-methylanthraquinone
  参考文献：
  名称：

  Total Synthesis, Cytotoxic Effects of Damnacanthal, Nordamnacanthal and Related Anthraquinone Analogues

  摘要：

  天然存在的蒽醌类化合物达米卡酸酮（damnacanthal, 1）和北达米卡酸酮（nordamnacanthal, 2）通过改进的反应步骤合成，并分别研究了它们对MCF-7和K-562癌细胞系的细胞毒性。中间类似物2-溴甲基-1,3-二甲氧基蒽醌（5，IC50 = 5.70 ± 0.21和8.50 ± 1.18 mg/mL）、2-羟甲基-1,3-二甲氧基蒽醌（6，IC50 = 12.10 ± 0.14和14.00 ± 2.13）、2-羰基-1,3-二甲氧基蒽醌（7，IC50 = 13.10 ± 1.02和14.80 ± 0.74）、1,3-二甲氧基-2-甲基蒽醌（4，IC50 = 9.40 ± 3.51和28.40 ± 2.33）、1,3-二羟基-2-甲基蒽醌（3，IC50 = 25.60 ± 0.42和28.40 ± 0.79）也在MCF-7和K-562癌细胞系中表现出适度的细胞毒性。其他结构相关的化合物，如1,3-二羟基蒽醌（13a，IC50 = 19.70 ± 0.35和14.50 ± 1.28）、1,3-二甲氧基蒽醌（13b，IC50 = 6.50 ± 0.66和5.90 ± 0.95），也表现出良好的细胞毒性。目标化合物达米卡酸酮（1）在MCF-7和K-562癌细胞系中被发现具有最高的细胞毒性，IC50值分别为3.80 ± 0.57和5.50 ± 1.26。所有化合物的结构通过详细的光谱技术得到了阐明。

  DOI：

  10.3390/molecules180810042

文献信息

• CCXXIII.—Syntheses of glucosides. Part V. Two new syntheses of rubiadin and syntheses of 1-O-methylrubiadin and of rubiadin glucoside
  作者：Elfed Thomas Jones、Alexander Robertson

  DOI：10.1039/jr9300001699

  日期：——