1,3-dimethoxy-2-ethoxymethylanthraquinone | 63965-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,3-dimethoxy-2-ethoxymethylanthraquinone
• 英文别名: 3-Methoxy-damnacantol-ω-ethylaether；Methoxy-ω-ethylether-damnacantol；2ω-O-Ethyl-1.3-O-dimethyl-lucidin；2-ethoxymethyl-1,3-dimethoxy-anthraquinone；2-Aethoxymethyl-1,3-dimethoxy-anthrachinon；2-(Ethoxymethyl)-1,3-dimethoxyanthracene-9,10-dione；2-(ethoxymethyl)-1,3-dimethoxyanthracene-9,10-dione
• CAS: 63965-58-2
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: YEIXBQLNJAGNKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-dimethoxy-2-ethoxymethylanthraquinone 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 、 溶剂黄146 作用下， 以 四氯化碳 、 水 为溶剂， 反应 48.0h， 以80%的产率得到1,3-dimethoxy-2-formylanthraquinone
  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：

  1-acetoxy-2-bromomethyl-3-methoxy-anthraquinone 在 sodium hydroxide 、 potassium carbonate 、 丙酮 作用下， 生成 1,3-dimethoxy-2-ethoxymethylanthraquinone
  参考文献：
  名称：

  Joshi et al., Journal Of Scientific and Industrial Research, 1955, vol. 14 B, p. 87,92

  摘要：

  DOI：