1,8-dihydroxy-10-(2-amino-2-carboxyethylthio)-9-anthrone | 107401-52-5

• 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-(2-amino-2-carboxyethylthio)-9-anthrone
• 英文别名: 2-Amino-3-(4,5-dihydroxy-10-oxo-9,10-dihydro-anthracen-9-ylsulfanyl)-propionic acid；2-amino-3-[(4,5-dihydroxy-10-oxo-9H-anthracen-9-yl)sulfanyl]propanoic acid
• CAS: 107401-52-5
• 化学式: C₁₇H₁₅NO₅S
• 分子量: 345.376
• InChiKey: PFHGBMLIIWQSFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  7

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-(2-amino-2-carboxyethylthio)-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

• Interaction of anthralin with cysteine: a new entry into the chemistry of biologically active anthrones.
  作者：M. d'Ischia、A. Privitera、G. Prota

  DOI：10.1016/s0040-4039(01)81533-1

  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.