1,3-dimethoxy-2-methylanthraquinone | 22170-88-3

• 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-methylanthraquinone
• 英文别名: rubiadin-dimethyl ether；rubiadin 1,3-dimethyl ether；1,3-dimethoxy-2-methyl-anthraquinone；1,3-Dimethoxy-2-methyl-anthrachinon；Rubiadin-1,3-dimethylaether；Rubiadin-dimethylaether；Rubiadin dimethyl ether；1,3-dimethoxy-2-methylanthracene-9,10-dione
• CAS: 22170-88-3
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: GFEPHBKJTZSEJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-dimethoxy-2-methylanthraquinone 在 Jones reagent 、 溶剂黄146 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 生成 茜草酸
  参考文献：
  名称：

  Synthesis of an anthraquinone derivative (DHAQC) and its effect on induction of G2/M arrest and apoptosis in breast cancer MCF-7 cell line

  摘要：

  Anthraquinones are an important class of naturally occurring biologically active compounds. In this study, anthraquinone derivative 1,3-dihydroxy-9,10-anthraquinone-2- carboxylic acid (DHAQC) (2) was synthesized with 32% yield through the Friedel-Crafts condensation reaction. The mechanisms of cytotoxicity of DHAQC (2) in human breast cancer MCF-7 cells were further investigated. Results from the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay showed that DHAQC (2) exhibited potential cytotoxicity and selectivity in the MCF-7 cell line, comparable with the naturally occurring anthraquinone damnacanthal. DHAQC (2) showed a slightly higher IC50 (inhibitory concentration with 50% cell viability) value in the MCF-7 cell line compared to damnacanthal, but it is more selective in terms of the ratio of IC50 on MCF-7 cells and normal MCF-10A cells. (selective index for DHAQC (2) was 2.3 and 1.7 for damnacanthal). The flow cytometry cell cycle analysis on the MCF-7 cell line treated with the IC50 dose of DHAQC (2) for 48 hours showed that DHAQC (2) arrested MCF-7 cell line at the G2/M phase in association with an inhibited expression of PLK1 genes. Western blot analysis also indicated that the DHAQC (2) increased BAX, p53, and cytochrome c levels in MCF-7 cells, which subsequently activated apoptosis as observed in annexin V/propidium iodide and cell cycle analyses. These results indicate that DHAQC (2) is a synthetic, cytotoxic, and selective anthraquinone, which is less toxic than the natural product damnacanthal, and which demonstrates potential in the induction of apoptosis in the breast cancer MCF-7 cell line.

  DOI：

  10.2147/dddt.s65468
• 作为产物：
  描述：

  3-羟基-1-甲氧基-2-甲基蒽醌 在 硫酸 、 potassium carbonate 、 丙酮 作用下， 反应 0.17h， 生成 1,3-dimethoxy-2-methylanthraquinone
  参考文献：
  名称：

  269. coprosma属的化学。第四部分 香附子的非糖苷蒽醌类化合物

  摘要：

  DOI：

  10.1039/jr9490001241

文献信息

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

  DOI：——

  日期：——
• 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：——
• 116. Chemistry of the Coprosma genus. Part I. The colouring matters from Coprosma australis
  作者：Lindsay H. Briggs、Jack C. Dacre

  DOI：10.1039/jr9480000564

  日期：——
• Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines
  作者：Koushik Saha、Kok Wai Lam、Faridah Abas、A. Sazali Hamzah、Johnson Stanslas、Lim Siang Hui、Nordin H. Lajis

  DOI：10.1007/s00044-012-0197-5

  日期：2013.5

  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.
• METHODS, COMPOSITIONS, AND KITS FOR THE TREATMENT OF CANCER
  申请人：Haggerty Timothy J.

  公开号：US20140335050A1

  公开（公告）日：2014-11-13

  The invention features methods, compositions, and kits for the administration of an HSP90 inhibitor, OBAA, flunarizine, aphidicolin, damnacanthal, dantrolene, or an analog thereof, alone, or in combination with, e.g., a TAA, an antigen-binding scaffold (e.g., an antibody, a soluble T cell receptor, or a chimeric receptor) specific for a TAA, a cell (e.g., a white blood cell that targets a cancer cell), and/or an IFN-β receptor agonist or an IFN-γ receptor agonist, for the treatment of cancer.