1,8-dihydroxy-10-<(3,4-dihydroxyphenyl)methylene>-9(10H)-anthracenone

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,8-dihydroxy-10-<(3,4-dihydroxyphenyl)methylene>-9(10H)-anthracenone
• 英文别名: 10-(3,4-Dihydroxy-benzylidene)-1,8-dihydroxy-10H-anthracen-9-one；10-(3,4-dihydroxybenzylidene)-1,8-dihydroxyanthracen-9(10H)-one；10-[(3,4-dihydroxyphenyl)methylidene]-1,8-dihydroxyanthracen-9-one
• 化学式: C₂₁H₁₄O₅
• 分子量: 346.339
• InChiKey: HAOIGARVPBUDHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  地蒽酚 在 camphor-10-sulfonic acid 作用下， 以 甲苯 为溶剂， 以28%的产率得到1,8-dihydroxy-10-<(3,4-dihydroxyphenyl)methylene>-9(10H)-anthracenone
  参考文献：
  名称：

  Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods

  摘要：

  细胞保护化合物，其中许多是酚类衍生物，其特点是具有特定共轭键的取代酚，对于治疗某些缺血或炎症性疾病非常有用，包括但不限于中风、心肌梗死、充血性心力衰竭以及以炎症或氧化损伤为特征的皮肤疾病。它们还可用于制造用于治疗这些疾病的药物和化妆品配方。

  公开号：

  US20030073712A1

文献信息

• Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase
  作者：Klaus Mueller、Dieter Guerster、Susanne Piwek、Wolfgang Wiegrebe

  DOI：10.1021/jm00077a015

  日期：1993.12

  The syntheses, the biological evaluation, and the structure-activity relationships of a novel series of 1,8-dihydroxy-9(10H)-anthracenones bearing acyl-, alkyl-, or alkylidene-linked aromatic substituents in the 10-position are described. The phenylacyl and phenylalkylidene analogs were far more potent inhibitors of 5-lipoxygenase (5-LO) from bovine polymorphonuclear leukocytes (IC50 values in the 10(-7) M range) than the antipsoriatic drug anthralin, whereas phenylalkyl analogs were only weak inhibitors. Among the active compounds were both potent generators of hydroxyl radicals, as determined by deoxyribose degradation, and strong reducers of the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). However, several derivatives of this series maintained 5-LO inhibitory activity but did not generate hydroxyl radicals and were not reactive with DPPH. In particular, phenylacyl analogs were also 6 times more efficient in inhibition of lipid peroxidation in model membranes than anthralin. Structure-activity relationships have shown that the presence of free phenolic groups in the attached aromatic ring is beneficial but not required for 5-LO inhibitory potency. The inhibitory potency in the 10-phenylacyl series increased with the length of the acyl chain with three methylene units being the optimum, suggesting a specific enzyme interaction which would not be expected for nonspecific redox inhibitors.
• Synthesis, antiproliferative activity and inhibition of tubulin polymerization by 1,5- and 1,8-disubstituted 10H-anthracen-9-ones bearing a 10-benzylidene or 10-(2-oxo-2-phenylethylidene) moiety
  作者：Holger C. Nickel、Peter Schmidt、Konrad J. Böhm、Silke Baasner、Klaus Müller、Matthias Gerlach、Eberhard Unger、Eckhard G. Günther、Helge Prinz

  DOI：10.1016/j.ejmech.2010.04.032

  日期：2010.8

  A novel series of 1,5- and 1,8-disubstituted 10-benzylidene-10H-anthracen-9-ones and 10-(2-oxo-2-phenylethylidene)-10H-anthracen-9-ones was synthesized to assess the substituent effects on biological activity. The 3-hydroxy-2,4-dimethoxy-benzylidene analogue 16h displayed strong antiproliferative activity against several tumor cell lines, including multi-drug resistant phenotypes. Flow cytometric studies showed that KB/HeLa cells treated by elected compounds were arrested in the G2/M phases of the cell cycle. Among the compounds tested for inhibition of tubulin polymerization, 14 compounds proved to be exceptionally active with IC50 values < 1 mu M. In the 1,5-dichloro-derived series of benzylideneanthracenones, E/Z isomers were separated and biological effects were monitored. We found that the olefinic geometry had no significant effect on biological activity. Furthermore, the E isomeric 1,5-dichloro-substituted phenacylidenes entirely proved to be more potent inhibitors of tubulin polymerization than the recently described 10-(2-oxo-2-phenylethylidene)-10H-anthracen-9-ones. In conclusion, the present study improves understanding of the action of anthracenone-based tubulin polymerization inhibitors and contributes to the design of further potent anti-tubulin drugs. (C) 2010 Elsevier Masson SAS. All rights reserved.
• 10-SUBSTITUTED 1,8-DIHYDROXY-9(10H) ANTHRACENONE PHARMACEUTICALS
  申请人：TEVA PHARMACEUTICAL INDUSTRIES LTD.

  公开号：EP0664780A1

  公开（公告）日：1995-08-02
• CYTOPROTECTIVE COMPOUNDS, PHARMACEUTICAL AND COSMETIC FORMULATIONS, AND METHODS
  申请人：Galileo Pharmaceuticals, Inc.

  公开号：EP1435894A2

  公开（公告）日：2004-07-14
• EP1435894A4
  申请人：——

  公开号：EP1435894A4

  公开（公告）日：2005-07-06