1,8-dihydroxy-10-<2-(4-hydroxyphenyl)-1-oxoethyl>-9(10H)-anthracenone | 151562-57-1

• 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-(4-hydroxyphenyl)-1-oxoethyl>-9(10H)-anthracenone
• 英文别名: 1,8-Dihydroxy-10-[2-(4-hydroxyphenyl)-1-oxoethyl]-9(10H)-anthracenone；1,8-Dihydroxy-10-[2-(4-hydroxy-phenyl)-acetyl]-10H-anthracen-9-one；1,8-dihydroxy-10-[2-(4-hydroxyphenyl)acetyl]-10H-anthracen-9-one
• CAS: 151562-57-1
• 化学式: C₂₂H₁₆O₅
• 分子量: 360.366
• InChiKey: QKVUGRSIFXNRPS-UHFFFAOYSA-N

物化性质

• 沸点：
  609.6±55.0 °C(Predicted)
• 密度：
  1.442±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,8-dihydroxy-10-<2-(4-hydroxyphenyl)-1-oxoethyl>-9(10H)-anthracenone 在 氧气 作用下， 以 乙醇 为溶剂， 反应 240.0h， 生成 对羟基苯乙酸 、 1,8-二羟基蒽醌
  参考文献：
  名称：

  10-取代的 1,8-二羟基-9 (10H)-蒽酮的酸度和稳定性

  摘要：

  测定了 10-取代蒽林衍生物在二甲亚砜和乙醇中的分解。虽然 10 - ω - 苯基亚烷基衍生物完全稳定，但 10 - ω - 苯基酰基取代的化合物缓慢降解为丹蒽酮和相应的羧酸。然而，与蒽林相比，这些衍生物的稳定性显着提高。pKa值的测定表明，ω-苯酰基衍生物比地蒽酚具有更强的酸，而ω-苯基亚烷基-取代通常使地蒽酚部分的酸度保持不变。

  DOI：

  10.1002/ardp.19953280412
• 作为产物：
  描述：

  地蒽酚 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 1,8-dihydroxy-10-<2-(4-hydroxyphenyl)-1-oxoethyl>-9(10H)-anthracenone
  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-SUBSTITUTED 1,8-DIHYDROXY-9(10H) ANTHRACENONE PHARMACEUTICALS
  申请人：TEVA PHARMACEUTICAL INDUSTRIES LTD.

  公开号：EP0664780A1

  公开（公告）日：1995-08-02
• US5426197A
  申请人：——

  公开号：US5426197A

  公开（公告）日：1995-06-20
• US5661187A
  申请人：——

  公开号：US5661187A

  公开（公告）日：1997-08-26
• US5844004A
  申请人：——

  公开号：US5844004A

  公开（公告）日：1998-12-01
• US5952390A
  申请人：——

  公开号：US5952390A

  公开（公告）日：1999-09-14