1,8-di-O-methylemodin | 5018-83-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,8-di-O-methylemodin
• 英文别名: questin；3-hydroxy-1,8-dimethoxy-6-methyl-anthraquinone；3-Hydroxy-1,8-dimethoxy-6-methyl-anthrachinon；Emodin-1,8-dimethylether；3-Hydroxy-1,8-dimethoxy-6-methylanthracene-9,10-dione
• CAS: 5018-83-7
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: OYZPCMARNWAKQF-UHFFFAOYSA-N

物化性质

• 熔点：
  285-295 °C (decomp)
• 沸点：
  531.1±50.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2'-diacetoxy-4,5,4',5'-tetramethoxy-7,7'-dimethyl-[1,1']bianthryl-9,10,9',10'-tetraone 在 sodium dithionite 作用下， 生成 1,8-di-O-methylemodin
  参考文献：
  名称：

  Tanaka, Chemical and pharmaceutical bulletin, 1958, vol. 6, p. 203,207

  摘要：

  DOI：

文献信息

• Antimutagenicity and Cytotoxicity of the Constituents from the Aerial Parts of Rumex acetosa
  作者：Nam-Jae Lee、Jung-Hyun Choi、Byung-Soo Koo、Shi-Yong Ryu、Yeong-Hwan Han、Seung-Il Lee、Dong-Ung Lee

  DOI：10.1248/bpb.28.2158

  日期：——

  Four anthraquinones isolated for the first time from the aerial parts of Rumex acetosa (Polygonaceae), a Korean and a Japanese medicinal plant, and two synthetic derivatives were examined for their cytotoxicities against five cultured human tumor cell lines, i.e. A549 (non-small cell lung), SK-OV-3 (ovary), SK-MEL-2 (melanoma), XF498 (central nerve system) and HCY15 (colon), using the Sulfrhodamine-B method in vitro and antimutagenic activities by Ames test with Salmonella typhimurium TA98 and TA100 and SOS chromotest with E. coli PQ37. Among the tested compounds, emodin strongly inhibited the proliferation of each examined tumor cell line with IC50 values ranged from 2.94 to 3.64 μg/ml and showed potent antimutagenic activities with 71.5% and 53.3% at the concentration of 0.1 mg/plate against the mutagens, NPD and sodium azide, respectively. Its antigenotoxic activity was also very effective at the final concentration of 10 μg/reaction tube against the mutagens, MNNG and NQO by SOS chromotest, reducing the induction factors by 19.6% and 43.5%, respectively. The structure–activity correlation study suggests that an additional OH group at C-6 position in the anthraquinone nucleus may play an important role for their cytotoxicities and an introduction of OH– or OCH3 group at C-6 position is necessary for their antimutagenicities.

  研究人员首次从韩国和日本药用植物蓼科植物鲁梅克斯（Rumex acetosa）的气生部分分离出四种蒽醌类化合物和两种合成衍生物，并采用 SGP 法检测了它们对五种培养的人类肿瘤细胞系（即 A549（非小细胞肺）、SK-OV-3（卵巢）、SK-MEL-2（黑色素瘤）、XF498（中枢神经系统）和 HCY15（结肠）的细胞毒性。体外采用磺胺-B 法检测了它们对 A549（非小细胞肺癌）、SK-OV-3（卵巢癌）、SK-MEL-2（黑色素瘤）、XF498（中枢神经系统）和 HCY15（结肠癌）等五种培养的人类肿瘤细胞株的细胞毒性，以及用伤寒沙门氏菌 TA98 和 TA100 进行的 Ames 试验和用大肠杆菌 PQ37 进行的 SOS 染色试验检测的抗突变活性。在受试化合物中，大黄素能强烈抑制每种受试肿瘤细胞系的增殖，其 IC50 值介于 2.94 至 3.64 μg/ml 之间；在 0.1 mg/plate 浓度下，大黄素对诱变剂 NPD 和叠氮化钠的抗突变活性分别为 71.5%和 53.3%。通过 SOS 染色试验，当最终浓度为 10 μg/reaction tube 时，它对诱变剂 MNNG 和 NQO 的抗原毒活性也非常有效，诱导因子分别降低了 19.6% 和 43.5%。结构-活性相关性研究表明，蒽醌核的 C-6 位上有一个额外的 OH 基团可能对它们的细胞毒性起重要作用，而在 C-6 位上引入 OH- 或 OCH3 基团是它们抗突变性的必要条件。
• 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.
• Tanaka, Chemical and pharmaceutical bulletin, 1958, vol. 6, p. 203,207
  作者：Tanaka

  DOI：——

  日期：——