6-bromomethyl-1,3,8-triacetoxyanthracene-9,10-dione | 84993-87-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 6-bromomethyl-1,3,8-triacetoxyanthracene-9,10-dione
• 英文别名: 1,3,8-triacetoxy-6-bromomethylanthraquinone；1,3,8-triacetoxy-6-bromomethyl-anthraquinone；1,3,8-Triacetoxy-6-brommethyl-anthrachinon；9,10-Anthracenedione, 1,3,8-tris(acetyloxy)-6-(bromomethyl)-；[4,5-diacetyloxy-7-(bromomethyl)-9,10-dioxoanthracen-2-yl] acetate
• CAS: 84993-87-3
• 化学式: C₂₁H₁₅BrO₈
• 分子量: 475.249
• InChiKey: JIFURIZGDKTTRD-UHFFFAOYSA-N

物化性质

• 沸点：
  642.3±55.0 °C(Predicted)
• 密度：
  1.576±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-bromomethyl-1,3,8-triacetoxyanthracene-9,10-dione 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 超重氢 、 氢气 作用下， 以 甲醇 为溶剂， 反应 8.5h， 生成 1,6,8-triacetoxy-3-<3H>methyl-9,10-anthraquinone
  参考文献：
  名称：

  高比放射性[3H]大黄素的合成

  摘要：

  大黄素是 Pyrenochaeta terrestris 生物合成 cynodontin 中大黄酚的前体，已通过溴甲基大黄素的氢解以高比放射性 (12.5 Ci/mmol) 氚化。

  DOI：

  10.1002/jlcr.2580360811
• 作为产物：
  描述：

  大黄素 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 苯 为溶剂， 反应 27.0h， 生成 6-bromomethyl-1,3,8-triacetoxyanthracene-9,10-dione
  参考文献：
  名称：

  A facile synthesis of emodin derivatives, emodin carbaldehyde, citreorosein, and their 10-deoxygenated derivatives and their inhibitory activities on μ-calpain

  摘要：

  该研究描述了一种制备大黄素甲醛和香茅苷的新方法，其中，ω,ω′-二溴甲基大黄素三乙酸酯是通过 NBS 介导的 1,3,8-三乙酰基大黄素溴化反应制备的关键中间体。在 1:1 的 HOAc 和 HCl 混合物中用 SnCl2 还原大黄素和香茅素，可分别得到 90% 和 92% 的相应蒽，而相应的 10-脱氧大黄素甲醛则是通过 MnO2 氧化 10-脱氧硝基香茅素制备的。10-Desoxycitreorosein 和大黄素甲醛显示出可行的μ-钙蛋白酶抑制活性，IC50 值分别为 20.15 和 25.77 M。

  DOI：

  10.1007/s12272-012-0307-4

文献信息

• Rajagopalan; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1956, vol. 44, p. 418,421
  作者：Rajagopalan、Seshadri

  DOI：——

  日期：——
• Novel anthraquinone inhibitors of human leukocyte elastase and cathepsin G
  作者：David E. Zembower、Chih Min Kam、James C. Powers、Leon H. Zalkow

  DOI：10.1021/jm00087a014

  日期：1992.5

  A large series of variously substituted anthraquinones has been synthesized and assayed for inhibitory capacity against human leukocyte elastase (HLE) and cathepsin G (CatG), two serine proteinases implicated in diseases characterized by the abnormal degradation of connective tissue, such as pulmonary emphysema and rheumatoid arthritis. It was found that 2-alkyl-1,8-dihydroxyanthraquinone analogues are competitive inhibitors of HLE with IC50 values ranging from 4 to 10-mu-M, and also inhibit CatG with IC50 values ranging from 25 to 55-mu-M. Consequently, analogues containing the 2-alkyl-1-hydroxy-8-methoxyanthraquinone substitution pattern inhibit HLE to the same magnitude as for the compounds above, but show very little inhibition of CatG. Anthraquinones containing long, hydrophobic n-butyl carbonate moieties in the 1- and 8-positions in conjunction with a third hydrophobic substituent in the 2- or 3-position are highly selective for HLE, with K(i) values in the range of 10(-7) M. All of the inhibitors described are completely reversible, with no evidence of acyl-enzyme formation detected.
• Characterization of emodin metabolites in Raji cells by LC–APCI-MS/MS
  作者：Junko Koyama、Atsuko Takeuchi、Izumi Morita、Yu Nishino、Maki Shimizu、Munetaka Inoue、Norihiro Kobayashi

  DOI：10.1016/j.bmc.2009.09.024

  日期：2009.11

  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.
• Thiem, Joachim; Wessel, Hans-Peter, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1985, vol. 40, # 3, p. 422 - 425
  作者：Thiem, Joachim、Wessel, Hans-Peter

  DOI：——

  日期：——
• Hirose, Yoshio; Suehiro, Yoshihisa; Furukawa, Yumiko, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 11, p. 4186 - 4188
  作者：Hirose, Yoshio、Suehiro, Yoshihisa、Furukawa, Yumiko、Murakami, Takao

  DOI：——

  日期：——