10-benzylthio-1,8-dihydroxy-9-anthrone | 107401-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 10-benzylthio-1,8-dihydroxy-9-anthrone
• 英文别名: 10-Benzylsulfanyl-1,8-dihydroxy-10H-anthracen-9-one
• CAS: 107401-53-6
• 化学式: C₂₁H₁₆O₃S
• 分子量: 348.422
• InChiKey: SVCCMVDKTSCNNB-UHFFFAOYSA-N

物化性质

• 熔点：
  153 °C(Solv: benzene (71-43-2))
• 沸点：
  554.8±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 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-benzylthio-1,8-dihydroxy-9-anthrone
  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。
• Electron-impact Induced and Thermal Decomposition of Dithranol Derivatives, II: Multiple H-Rearrangements in 10-Benzylthio-dithranol Radical Cations Elektronenstoß-induzierter und thermischer Zerfall von Dithranol Derivaten, 2. Mitt.: Mehrfache H-Umlagerungen in den Molekülionen des 10-Benzylthio-dithranols
  作者：Hsu-Shan Huang、Wolfgang Wiegrebe、Klaus K. Mayer

  DOI：10.1002/ardp.19943271110

  日期：——
• DISCHIA, M.;PROTA, G., SYNTHESIS, BRD, 1986, N 5, 430-431
  作者：DISCHIA, M.、PROTA, G.

  DOI：——

  日期：——
• Antipsoriatic Anthrones with Modulated Redox Properties. 3. 10-Thio-Substituted 1,8-Dihydroxy-9(10<i>H</i>)-anthracenones as Inhibitors of Keratinocyte Growth, 5-Lipoxygenase, and the Formation of 12(<i>S</i>)-HETE in Mouse Epidermis
  作者：Klaus Müller、Hsu-Shan Huang、Wolfgang Wiegrebe

  DOI：10.1021/jm960259l

  日期：1996.1.1

  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.