10-benzylanthralin

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 10-benzylanthralin
• 英文别名: 10-benzyl-1,8-dihydroxy-10H-anthracen-9-one
• 化学式: C₂₁H₁₆O₃
• 分子量: 316.356
• InChiKey: VYKRRJBOIVZQKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  地蒽酚 、 氯化苄 在 sodium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以20%的产率得到10-benzylanthralin
  参考文献：
  名称：

  Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase

  摘要：

  The syntheses, the biological evaluation, and the structure-activity relationships of a novel series of 1,8-dihydroxy-9(10H)-anthracenones bearing acyl-, alkyl-, or alkylidene-linked aromatic substituents in the 10-position are described. The phenylacyl and phenylalkylidene analogs were far more potent inhibitors of 5-lipoxygenase (5-LO) from bovine polymorphonuclear leukocytes (IC50 values in the 10(-7) M range) than the antipsoriatic drug anthralin, whereas phenylalkyl analogs were only weak inhibitors. Among the active compounds were both potent generators of hydroxyl radicals, as determined by deoxyribose degradation, and strong reducers of the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). However, several derivatives of this series maintained 5-LO inhibitory activity but did not generate hydroxyl radicals and were not reactive with DPPH. In particular, phenylacyl analogs were also 6 times more efficient in inhibition of lipid peroxidation in model membranes than anthralin. Structure-activity relationships have shown that the presence of free phenolic groups in the attached aromatic ring is beneficial but not required for 5-LO inhibitory potency. The inhibitory potency in the 10-phenylacyl series increased with the length of the acyl chain with three methylene units being the optimum, suggesting a specific enzyme interaction which would not be expected for nonspecific redox inhibitors.

  DOI：

  10.1021/jm00077a015

文献信息

• 10-ω-Phenylalkyl-9(10H)-anthracenones as inhibitors of keratinocyte growth with reduced membrane damaging properties
  作者：Klaus Müller、Klaus Breu

  DOI：10.1016/s0960-894x(98)00580-0

  日期：1998.11

  Work aimed at further improving the benefit to risk ratio of the antipsoriatic agent anthralin has led to 10-omega-phenylalkyl-9(10H)-anthracenones, members of which are equally potent as inhibitors of the growth of HaCaT keratinocytes. In contrast to anthralin, induction of membrane injury is strongly reduced as documented by the release of LDH activity from cytoplasm of keratinocytes. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase
  作者：Klaus Mueller、Dieter Guerster、Susanne Piwek、Wolfgang Wiegrebe

  DOI：10.1021/jm00077a015

  日期：1993.12

  The syntheses, the biological evaluation, and the structure-activity relationships of a novel series of 1,8-dihydroxy-9(10H)-anthracenones bearing acyl-, alkyl-, or alkylidene-linked aromatic substituents in the 10-position are described. The phenylacyl and phenylalkylidene analogs were far more potent inhibitors of 5-lipoxygenase (5-LO) from bovine polymorphonuclear leukocytes (IC50 values in the 10(-7) M range) than the antipsoriatic drug anthralin, whereas phenylalkyl analogs were only weak inhibitors. Among the active compounds were both potent generators of hydroxyl radicals, as determined by deoxyribose degradation, and strong reducers of the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). However, several derivatives of this series maintained 5-LO inhibitory activity but did not generate hydroxyl radicals and were not reactive with DPPH. In particular, phenylacyl analogs were also 6 times more efficient in inhibition of lipid peroxidation in model membranes than anthralin. Structure-activity relationships have shown that the presence of free phenolic groups in the attached aromatic ring is beneficial but not required for 5-LO inhibitory potency. The inhibitory potency in the 10-phenylacyl series increased with the length of the acyl chain with three methylene units being the optimum, suggesting a specific enzyme interaction which would not be expected for nonspecific redox inhibitors.