1,3-dimethoxy-2-formylanthraquinone | 4480-87-9

• 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-formylanthraquinone
• 英文别名: 2-formyl-1,3-dimethoxyanthraquinone；1,3-Dimethoxy-9,10-dioxoanthracene-2-carbaldehyde
• CAS: 4480-87-9
• 化学式: C₁₇H₁₂O₅
• 分子量: 296.279
• InChiKey: ULIAIGCCXMQZGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.7
• 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-formylanthraquinone 在 aluminum (III) chloride 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以28%的产率得到1,3-二羟基-9,10-二氧代蒽-2-甲醛
  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
• 作为产物：
  描述：

  2-hydroxymethyl-1,3-dimethoxy-9,10-anthraquinone 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 生成 1,3-dimethoxy-2-formylanthraquinone
  参考文献：
  名称：

  Castonguay,A.; Brassard,P., Canadian Journal of Chemistry, 1977, vol. 55, p. 1324 - 1332

  摘要：

  DOI：

文献信息

• Anthraquinones from Neonauclea calycina and Their Inhibitory Activity against DNA Topoisomerase II.
  作者：Hideki TOSA、Munekazu IINUMA、Fujio ASAI、Toshiyuki TANAKA、Hiroshi NOZAKI、Shougo IKEDA、Ken TSUTSUI、Kimiko TSUTSUI、Masashi YAMADA、Shiho FUJIMORI

  DOI：10.1248/bpb.21.641

  日期：——

  In a series of searches fot DNA topoisomerase II inhibitors from naturally occurring compounds, a wood extract of Neonauclea calycina MERR. (Rubiaceae) showed a moderate effect in vitro. Purification of the extract resulted in the isolation of seven known anthraquinones. The structures were characterized as damnacanthal, rubiadin 1-methyl ether, nordamnacanthal, morindone, damnacanthol, lucidin 3-O-primeveroside and morindone 6-O-primeveroside by spectral analysis, respectively. Damnacanthal and morindone showed an intensive inhibitory effect against topoisomerase II (IC50 : 20μg/ml and 21μg/ml).

  在一系列从天然化合物（Neonauclea calycina MERR 的木材提取物）中寻找 DNA 拓扑异构酶 II 抑制剂的过程中。 （茜草科）在体外表现出中等效果。提取物的纯化导致七种已知的蒽醌的分离。通过光谱分析，其结构分别为damacanthal、rubiadin 1-methyl ether、nordamnacanthal、morindone、damacanthol、lucidin 3-O-primeveroside和morindone 6-O-primeveroside。 Damnacanthal 和吗啉酮对拓扑异构酶 II 显示出强烈的抑制作用（IC50：20μg/ml 和 21μg/ml）。
• Chemistry of Damnacanthus Genus. V. Some Derivatives of Damnacanthal-Munjistin Dimethyl Ether.
  作者：Susumu Nonomura

  DOI：10.1248/cpb1953.5.366

  日期：——

  Methylation of damnacanthal with diazomethane gave a methyl ketone derivative, while methylation with dimethyl sulfate and anhydrous potassium carbonate gave a monomethy ether and munjistin dimethyl ether (m.p. 263∼265°), and methylation with methyl iodide and silver oxide gave a trimethyl ether. The infrared absorption spectra of these methyl derivatives and other derivatives of damnacanthal were measured.

  用重氮甲烷甲基化可得到甲基酮衍生物，用硫酸二甲酯和无水碳酸钾甲基化可得到一甲基醚和门冬酰胺二甲醚（m.p. 263∼265°），用甲基碘和氧化银甲基化可得到三甲基醚。测量了这些甲基衍生物和达玛坎塔醛其他衍生物的红外吸收光谱。
• 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.

表征谱图