10-苯基硫代-1,8-二羟基-9-蒽酮 | 107401-55-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 10-苯基硫代-1,8-二羟基-9-蒽酮
• 英文名称: 10-phenylthio-1,8-dihydroxy-9-anthrone
• 英文别名: 1,8-Dihydroxy-10-phenylsulfanyl-10H-anthracen-9-one
• CAS: 107401-55-8
• 化学式: C₂₀H₁₄O₃S
• 分子量: 334.395
• InChiKey: XZHKFWSUJHGOSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10-苯基硫代-1,8-二羟基-9-蒽酮 反应 0.5h， 生成 地蒽酚 、 10-(4,5-二羟基-10-氧代-9H-蒽-9-基)-1,8-二羟基-10H-蒽-9-酮 、 苯硫酚 、 二苯二硫醚 、 1,8-Dihydroxy-10,10-bis-phenylsulfanyl-10H-anthracen-9-one 、 4,5,4',5'-Tetrahydroxy-9-phenylsulfanyl-9H,9'H-[9,9']bianthracenyl-10,10'-dione
  参考文献：
  名称：

  Dithranol 衍生物的电子撞击诱导和热分解，I：质谱仪中 10-苯硫基-二蒽醇的热解。dithranol 衍生物的电子碰撞诱导和热分解，第 1 次出版物：质谱仪中 10-苯硫基二蒽醇的热解

  摘要：

  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)。

  DOI：

  10.1002/ardp.19943271013
• 作为产物：
  描述：

  地蒽酚 在 溴 、 三氟乙酸 作用下， 以 二硫化碳 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 10-苯基硫代-1,8-二羟基-9-蒽酮
  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

• Synthesis of 10-Alkylthio- and Arylthio-1,8-Dihydroxy-9-anthrones, A New Class of Anthracene Derivatives of Potential Pharmacological Interest
  作者：Marco d'Ischia、Giuseppe Prota

  DOI：10.1055/s-1986-31668

  日期：——

  The synthesis of some representative 10-alkylthio- and 10-arylthio-1, 8-dihydroxy-9-anthrones, a new class of anthracene derivatives of potential pharmacological interest, is described, involving acid-catalyzed reaction of 1,8,10-trihydroxy-9-anthrone with a thiol at room temperature. The easy availability of all intermediates and the mild reaction conditions render the method simple and of general application.

  本文描述了具有潜在药理作用的新一类蒽衍生物——10-烷基硫基和10-芳基硫基-1,8-二羟基-9-蒽酮的合成，涉及1,8,10-三羟基-9-蒽酮与硫醇在室温下进行的酸催化反应。所有中间体易于获得，反应条件温和，使该方法简单易行且具有普遍适用性。
• 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。
• DISCHIA, M.;PROTA, G., SYNTHESIS, BRD, 1986, N 5, 430-431
  作者：DISCHIA, M.、PROTA, G.

  DOI：——

  日期：——
• NEW COMPOUNDS OF THE ANTHRAQUINONE SERIES
  申请人：THE VICTORIA UNIVERSITY OF MANCHESTER

  公开号：EP0386050A1

  公开（公告）日：1990-09-12