10-溴-1,8-二羟基-10H-蒽-9-酮 | 2891-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 10-溴-1,8-二羟基-10H-蒽-9-酮
• 英文名称: 10-bromo-1,8-dihydroxy-9(10H)-anthracenone
• 英文别名: 10-Bromo-1,8-dihydroxy-10H-anthracen-9-one
• CAS: 2891-30-7
• 化学式: C₁₄H₉BrO₃
• 分子量: 305.128
• InChiKey: JXHWADZWXKBZAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-溴-1,8-二羟基-10H-蒽-9-酮 在 DL-半胱氨酸 作用下， 生成 1,8-二羟基蒽醌
  参考文献：
  名称：

  Interaction of anthralin with cysteine: a new entry into the chemistry of biologically active anthrones.

  摘要：

  DOI：

  10.1016/s0040-4039(01)81533-1
• 作为产物：
  描述：

  地蒽酚 在 溴 作用下， 以 二硫化碳 为溶剂， 生成 10-溴-1,8-二羟基-10H-蒽-9-酮
  参考文献：
  名称：

  Antipsoriatic Anthrones with Modulated Redox Properties. 3. 10-Thio-Substituted 1,8-Dihydroxy-9(10H)-anthracenones as Inhibitors of Keratinocyte Growth, 5-Lipoxygenase, and the Formation of 12(S)-HETE in Mouse Epidermis

  摘要：

  The synthesis of a series of 1,8-dihydroxy-9(10H)-anthracenones bearing sulfur-linked substituents in the 10-position is described. These compounds were evaluated for their ability to inhibit the growth of the human keratinocyte cell line HaCaT and the 5- and 12-lipoxygenase enzymes in bovine polymorphonuclear leukocytes and mouse epidermal homogenate, respectively. In addition, the following redox properties of the compounds were determined: reactivity against 2,2-diphenyl-1-picrylhydrazyl, generation of hydroxyl radicals as measured by deoxyribose degradation, and inhibition of lipid peroxidation in model membranes. Compounds 4e and 4h of this series compare favorably in the cellular assays with the antipsoriatic anthralin. They have the combined inhibitory action against leukotriene B-4 and 12(S)-HETE formation and are highly potent antiproliferative agents against keratinocyte growth. In contrast to anthralin, 4h, 1,8-dihydroxy-10-[(4-hydroxyphenyl)thiol]-9(10H)-anthracenone, is not cytotoxic as documented by the LDH activity released from cytoplasm of keratinocytes and does not enhance lipid peroxidation in model membranes.

  DOI：

  10.1021/jm960259l

文献信息

• Structure and tumor-promoting activity of analogs of anthralin (1,8-dihydroxy-9-anthrone)
  作者：B. L. Van Duuren、A. Segal、S. S. Tseng、G. M. Rusch、G. Loewengart、U. Mate、D. Roth、A. Smith、S. Melchionne、I. Seidman

  DOI：10.1021/jm00199a005

  日期：1978.1

  10-dihydroanthracene, and myristoyljuglone. All compounds were used in pure form for the bioassays. Of the 17 test compounds four showed notable tumor-promoting activity. They are 1,8-dihydroxy-10-acetyl-9-anthrone, 1,8-dihydroxy-10-myristoyl-9-anthrone, 1-hydroxy-9-anthrone, and juglone. In order to determine whether there is any relationship between tumor-promoting activity and metal chelation in this series

  在单次应用亚致癌剂量的7,12-二甲基苯并[蒽]蒽后，通过使用雌性ICR / Ha Swiss小鼠在小鼠皮肤上重复皮肤应用，测试了肿瘤促进剂anthralin的17种类似物的相同生物学特性。测试的化合物中有七个是新化合物。它们是1,8-二乙酰氧基-9-蒽酮，1,8-二肉豆蔻酰氧基-9-蒽酮，1,8-二羟基-10-乙酰基-9-蒽酮，1,8-二羟基-10-肉豆蔻酰基-9-蒽酮， 1,8,10-三羟基-9-蒽酮，1,8-二羟基-9,10-二氢蒽和肉豆蔻酰juglone。所有化合物均以纯净形式用于生物测定。在17种测试化合物中，有4种显示出明显的促肿瘤活性。它们是1,8-二羟基-10-乙酰基-9-蒽酮，1,8-二羟基-10-肉豆蔻酰基-9-蒽酮，1-羟基-9-蒽酮和juglone。为了确定在该系列中促进肿瘤的活性与金属螯合之间是否存在任何关系，使用二价金属离子Cu（II），Zn（）检测了蒽林及其非活性类似物1
• Electron-impact Induced and Thermal Decomposition of Dithranol Derivatives, I: Thermolysis of 10-Phenylthio-dithranol in the Mass Spectrometer. Elektronenstoß-induzierter und thermischer Zerfall von Dithranol Derivaten, 1. Mitt.: Thermolyse von 10-Phenylthio-dithranol im Massenspektrometer
  作者：Hsu-Shan Huang、Klaus K. Mayer、Wolfgang Wiegrebe

  DOI：10.1002/ardp.19943271013

  日期：——

  Dithranol (anthralin; 1,8‐dihydroxy‐9‐anthrone) and its derivatives bearing a variety of substituents in the 10‐position are of actual interest in research on psoriasis1). In connection herewith 10‐alkylthio‐and 10‐arylthio‐ 1,8‐dihydroxy‐9(10H)‐anthracenones were synthetized and used for antipsoriatic activity2,3).

  Dithranol（蒽林；1,8-二羟基-9-蒽酮）及其在 10-位带有多种取代基的衍生物在银屑病研究中具有实际意义1)。与此相关的 10-烷硫基-和 10-芳硫基-1,8-二羟基-9 (10H)-蒽酮被合成并用于抗银屑病活性2,3)。
• Compounds of the anthraquinone series
  申请人：The Victoria University of Manchester

  公开号：US04927845A1

  公开（公告）日：1990-05-22

  Anthralin analogues containing a thio-substituent, especially in one or more of the positions 2-, 7- and 10- of the anthralin ring. They may be made by reacting an anthralin derivative (e.g. 10-bromoanthralin) with a thiol or a compound containing a group convertible to a thio-group. Alternatively, a 1,8-dihydroxy anthraquinone containing a thio-substituent may be reduced. Reactive intermediates may be made by introducing one or more nuclear allylic groups into a 1,8-dihydroxy anthraquinone and then converting them into a reactive form, e.g. by epoxidation or halide addition. The intermediate can then reduced to the oxidation state corresponding to anthralin. Additional products having the 10-carbon atom of the anthralin ring as part of a heterocyclic ring, may be made by anthralins containing various substitutes thioalkyl groups as the 10-substituent. The compounds are useful for treatment of psoriasis, and may be formulated in the conventional vehicles for topical application, for example petrolatum.

  含有硫取代基的蒽醌类似物，尤其是在蒽醌环的2-、7-和10-位置中的一个或多个位置。它们可以通过将蒽醌衍生物（例如10-溴蒽醌）与硫醇或含有可转化为硫基团的化合物反应而制得。另外，含有硫取代基的1,8-二羟基蒽醌可以被还原。通过将一个或多个核联烯基引入1,8-二羟基蒽醌中，然后将其转化为反应性形式（例如通过环氧化或卤素加成），可以制备反应性中间体。然后，中间体可以还原为对应于蒽醌的氧化状态。含有各种硫代烷基取代基作为10-取代基的蒽醌可以制备成将蒽醌环的10-碳原子作为杂环的部分的其他产物。这些化合物可用于治疗牛皮癣，并可以制成传统的局部应用载体，例如凡士林。
• New compounds of the anthraquinone series
  申请人：THE VICTORIA UNIVERSITY OF MANCHESTER

  公开号：EP0314405A1

  公开（公告）日：1989-05-03

  Anthralin analogues containing a thio-substituent, especially in one or more of the positions 2-, 7- and 10- of the anthralin ring. They may be made by reacting an anthralin derivative (e.g. 10-bromoanthralin) with a thiol or a compound containing a group convertible to a thio-group. Alternatively, a 1,8-dihydroxy anthraquinone containing a thio-substituent may be reduced. Reactive intermediates may be made by introducing one or more nuclear allylic groups into a 1,8-dihydroxy anthraquinone and then converting them into a reactive form, e.g. by epoxidation or halide addition. The intermediate can then reduced to the oxidation state corresponding to anthralin. Additional products having the 10-carbon atom of the anthralin ring as part of a heterocyclic ring, may be made by anthralins containing various substitutes thioalkyl groups as the 10-substituent. The compounds are useful for treatment of psoriasis, and may be formulated in the conventional vehicles for topical application, for example petrolatum.

  含有硫代基团，特别是在蒽环的 2-、7-和 10-位中的一个或多个位置上的硫代基团的蒽林类似物。它们可以通过蒽林衍生物（如 10-溴蒽林）与硫醇或含有可转化为硫代基团的化合物反应制成。另外，还可以还原含有硫代基团的 1,8-二羟基蒽醌。在 1,8-二羟基蒽醌中引入一个或多个核烯丙基，然后通过环氧化或卤化物加成等方法将其转化为活性形式，即可制成反应中间体。然后，中间体可还原成与蒽林相对应的氧化态。 蒽环的 10 个碳原子作为杂环的一部分，可以通过含有各种取代硫代烷基作为 10-取代基的蒽制成其他产品。 这些化合物可用于治疗牛皮癣，并可配制成传统的外用载体，例如凡士林。
• Electron-Impact Induced and Thermal Decomposition of Dithranol Derivatives, III: Fragmentations of 10-Alkoxy- and 10-Benzyloxydithranol Radical Cations
  作者：Hsu-Shan Huang、Klaus K. Mayer、Wolfgang Wiegrebe

  DOI：10.1002/ardp.19953280319

  日期：——