3-Bromomethyl-1,8-dihydroxy-6-methoxy-9,10-anthraquinone | 121210-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-Bromomethyl-1,8-dihydroxy-6-methoxy-9,10-anthraquinone
• 英文别名: 3-(Bromomethyl)-1,8-dihydroxy-6-methoxyanthracene-9,10-dione
• CAS: 121210-64-8
• 化学式: C₁₆H₁₁BrO₅
• 分子量: 363.164
• InChiKey: LGADVNQDDJUGOR-UHFFFAOYSA-N

物化性质

• 熔点：
  249-250 °C
• 沸点：
  615.6±55.0 °C(Predicted)
• 密度：
  1.734±0.06 g/cm3(Predicted)

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：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Bromomethyl-1,8-dihydroxy-6-methoxy-9,10-anthraquinone 在 乙酸酐 、 potassium hydroxide 作用下， 生成 迷人醇
  参考文献：
  名称：

  Characterization of emodin metabolites in Raji cells by LC–APCI-MS/MS

  摘要：

  A rapid, simple, and sensitive liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry (LC-APCI-MS/MS) method was developed for the identification and quantification of emodin metabolites in Raji cells, using aloe-emodin as an internal standard. Analyses were performed on an LC system employing a Cosmosil 5C(18) AR-II column and a stepwise gradient elution with methanol-20 mM ammonium formate at a flow rate of 1.0 mL/min operating in the negative ion mode. As a result, the starting material emodin and its five metabolites were detected by analyzing extracts of Raji cells that had been cultivated in the presence of emodin. The identification of the metabolites and elucidation of their structures were performed by comparing their retention times and spectral patterns with those of synthetic samples. In addition to the major metabolite 8-O-methylemodin, four other metabolites were assigned as omega-hydroxyemodin, 3-O-methyl-omega-hydroxyemodin, 3-O-methylemodin (physcion), and chrysophanol. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.024
• 作为产物：
  描述：

  6-Bromomethyl-1,3,8-trimethoxy-6-methyl-anthraquinone 在 氢溴酸 、 溶剂黄146 作用下， 生成 3-Bromomethyl-1,8-dihydroxy-6-methoxy-9,10-anthraquinone
  参考文献：
  名称：

  具有共价键形成能力的插层剂。一种新型的潜在抗癌药。2.香豆酚和大黄素的衍生物。

  摘要：

  制备了蒽醌chsophophanol和大黄素或它们的各种甲基醚的五十一种新的C-甲基修饰的衍生物，用于研究对小鼠白血病L1210和人白血病HL-60细胞的抗癌活性的结构-活性关系。用分光光度法研究了代表性化合物与天然和变性DNA相互作用的能力。通常，具有氨基功能的那些蒽醌与DNA相互作用。1,8-二甲氧基蒽醌不能嵌入DNA。但是，1-或8-单羟基单甲氧基蒽醌与DNA有一定程度的相互作用。分光光度法研究的化合物的DNA亲和力数据与细胞毒性作用之间没有明显的直接相关性。当在暴露的最初30分钟内抑制[3H] TdR掺入DNA中时，这些化合物在72小时内对细胞生长的抑制作用的细胞毒作用与它们的作用成反比。出人意料的是，一些显示出更高细胞毒性的化合物没有抑制初始TdR掺入（0-30分钟），而其他一些强烈抑制TdR掺入的化合物最初在72 h内没有细胞毒性。结果表明，这些化合物产生的细胞毒性是时间依赖性

  DOI：

  10.1021/jm00127a032

文献信息

• 具有抗癌活性的大黄素单链双季铵盐及其制备 方法
  申请人：福州大学

  公开号：CN104356014B

  公开（公告）日：2016-03-30

  本发明公开了一种具有抗癌活性的大黄素单链双季铵盐及其制备方法，其为双保护6位大黄素双季铵盐或双脱保护6位大黄素双季铵盐；是将1,4-二碘丁烷与甲基双辛基叔胺或甲基双癸基叔胺反应，得到碘丁基季铵盐；将双保护溴代大黄素或双脱保护溴代大黄素与二甲胺反应，得到双保护大黄素叔胺或双脱保护大黄素叔胺，再将其与碘丁基季铵盐发生亲核取代反应，得到所述大黄素单链双季铵盐。体外癌细胞抑制试验表明，所得大黄素单链双季铵盐均具有良好的抗癌活性，其中双脱保护6位大黄素双季铵盐可有效抑制肝癌HepG2的生长，且对正常细胞毒副作用较小，证明大黄素单链双季铵盐可作为抗恶性肿瘤的药物，尤其适于肝癌的治疗，具有较大的应用前景。
• Synthesis, SAR and pharmacological characterization of novel anthraquinone cation compounds as potential anticancer agents
  作者：Yanyan Zheng、Li Zhu、Lulu Fan、Wenna Zhao、Jianlong Wang、Xianxiao Hao、Yunhui Zhu、Xiufang Hu、Yaofeng Yuan、Jingwei Shao、Wenfeng Wang

  DOI：10.1016/j.ejmech.2016.10.012

  日期：2017.1

  study, a series of novel quaternary ammonium salts of emodin, anthraquinone and anthrone were synthesized and their anticancer activities were tested in vitro. The effects of emodin quaternary ammonium salts on cell viability, apoptosis, intracellular ROS, and mitochondrial membrane potential were investigated in A375, BGC-823, HepG2 and HELF cells. The results demonstrated that compound 4a induced morphological

  大黄素（Emodin）是一种从大黄（Rheum palmatum L.）分离的天然蒽醌衍生物，具有良好的抗癌作用。在这项研究中，合成了大黄素，蒽醌和蒽酮的一系列新型季铵盐，并在体外测试了它们的抗癌活性。在A375，BGC-823，HepG2和HELF细胞中研究了大黄素季铵盐对细胞活力，细胞凋亡，细胞内ROS和线粒体膜电位的影响。结果表明化合物4a诱导了形态变化并降低了细胞活力。使用DAPI染色和Annexin V-FITC / PI染色观察化合物4a触发的凋亡。化合物4aP53和Caspase-3的上调显示，A375诱导的A375细胞凋亡与线粒体膜电位（ΔΨm）的耗散有关。用大黄素衍生物处理癌细胞后，它们产生活性氧（ROS）的能力显着提高，线粒体膜电位降低。另外，共聚焦显微镜测定法证实化合物4a主要位于A375细胞的线粒体中。这些结果表明化合物4a具有用于癌症治疗的潜力。
• Synthesis and antitumor activity of emodin quaternary ammonium salt derivatives
  作者：Jingwei Shao、Fengsen Zhang、Zedong Bai、Conghui Wang、Yaofeng Yuan、Wenfeng Wang

  DOI：10.1016/j.ejmech.2012.07.047

  日期：2012.10

  A series of new emodin derivatives modified at the C-3 and the C-6 positions were synthesized, and evaluated for their anticancer activities in vitro and in vivo. Among them, Compounds 5g and 5h had more significant antiproliferative ability against HepG2, BGC-823, AGS cancer cell lines and low cytotoxicity to HELF normal cell line, respectively. Compounds 5g and 5h induced AGS cell cycle arrest at G0/G1 phase and induce apoptosis via activation of caspase-3 and caspase-9 enzyme. In vivo studies using H22 xenografts in Kunming mice were conducted with 5g and 5h. The results revealed that the medium dosage group (10 mg/kg) of 5g and the high dosage group (25 mg/kg) of 5h showed significant antitumor activity compared to the control group. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Studies in anthracycline synthesis: simple Diels-Alder routes to pachybasin, .omega.-hydroxypachybasin, aloe-emodin, and fallacinol
  作者：Nicholas Benfaremo、Michael P. Cava

  DOI：10.1021/jo00201a033

  日期：1985.1
• KOYAMA, MASAO;TAKAHASHI, KIYOBUMI;CHOU, TING-CHAO;DARZYNKIEWICZ, ZBIGNIEW+, J. MED. CHEM., 32,(1989) N, C. 1594-1599
  作者：KOYAMA, MASAO、TAKAHASHI, KIYOBUMI、CHOU, TING-CHAO、DARZYNKIEWICZ, ZBIGNIEW+

  DOI：——

  日期：——