1,8-dihydroxy-10-[(4-hydroxyphenyl)thio]-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-[(4-hydroxyphenyl)thio]-9(10H)-anthracenone
• 英文别名: 1,8-Dihydroxy-10-(4-hydroxy-phenylsulfanyl)-10H-anthracen-9-one；1,8-dihydroxy-10-(4-hydroxyphenyl)sulfanyl-10H-anthracen-9-one
• 化学式: C₂₀H₁₄O₄S
• 分子量: 350.395
• InChiKey: RDAMJAZCJDHAJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 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：
  103
• 氢给体数：
  3
• 氢受体数：
  5

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 1,8-dihydroxy-10-[(4-hydroxyphenyl)thio]-9(10H)-anthracenone
  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

• [EN] 10-THIO-SUBSTITUTED 1,8-DIHYDROXY-9(10H)-ANTHRACENONE DERIVATIVES FOR USE IN THE TREATMENT OF INFLAMMATORY CONDITIONS<br/>[FR] DERIVES DE 1,8-DIHYDROXY-9(10H)-ANTHRACENONES THIO-SUBSTITUEES EN POSITION 10 DESTINES AU TRAITEMENT D'ETATS INFLAMMATOIRES
  申请人：TEVA PHARMACEUTICAL INDUSTRIES LTD.

  公开号：WO1996040632A1

  公开（公告）日：1996-12-19

  (EN) 10-Thio-substituted 1,8-dihydroxy-9(10H)-anthracenones of formula (III), in which R represents a substituted alkyl group or a substituted phenyl group which is useful in the treatment of inflammatory conditions, especially psoriasis.(FR) La présente invention concerne des 1,8-dihydroxy-9(10H)-anthracénones à substitution thio en position 10 qui sont représentées par la formule (III), dans laquelle R représente un groupe alkyle substitué ou un groupe phényle substitué, et qui s'avèrent utiles dans le traitement d'états inflammatoires, et notamment du psoriasis.

  该发明涉及到1,8双羟基-9(10H)-闪酸类化合物的第10位硫代基衍生物（用公式(III)表示，其中R代表取代的甲基或苯基，这些化合物在治疗炎症性疾病，尤其是湿疹中有用。其法语原文为：La présente invention concerne des 1,8-dihydroxy-9(10H)-anthracénones à substitution thio en position 10 qui sont représentées par la formule (III), dans laquelle R représente un groupe alkyle substitué ou un groupe phényle substitué, et qui s'avèrent utiles dans le traitement d'états inflammatoires, et notamment du psoriasis.)
• 10-THIO-SUBSTITUTED 1,8-DIHYDROXY-9(10H)-ANTHRACENONE DERIVATIVES FOR USE IN THE TREATMENT OF INFLAMMATORY CONDITIONS
  申请人：Teva Pharmaceutical Industries Limited

  公开号：EP0846103A1

  公开（公告）日：1998-06-10
• US5705533A
  申请人：——

  公开号：US5705533A

  公开（公告）日：1998-01-06
• 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.