E-1,8-dihydroxy-10-[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]-9(10H)-anthracenone

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: E-1,8-dihydroxy-10-[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]-9(10H)-anthracenone
• 英文别名: 1,8-dihydroxy-10-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-10H-anthracen-9-one
• 化学式: C₂₄H₁₈O₆
• 分子量: 402.403
• InChiKey: TWLPTGPMNOLZDQ-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  阿魏酸 、 地蒽酚 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以7%的产率得到E-1,8-dihydroxy-10-[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]-9(10H)-anthracenone
  参考文献：
  名称：

  10-Hydrocinnamoyl- and 10-cinnamoyl-1,8-dihydroxy-9(10H)-anthracenones as inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth

  摘要：

  A series of 10-hydrocinnamoyl and 10-cinnamoyl-1,8-dihydroxy-9(10H)-anthracenones has been synthesized and evaluated as inhibitors of leukotriene B-4 (LTB4) biosynthesis and as antiproliferative agents. In the hydrocinnamoyl series, compounds with phenolic hydroxyl groups were less potent inhibitors of LTB4 biosynthesis than their non-phenolic analogs, suggesting that a nonspecific redox interaction between the compounds and the active site Fe3+ of 5-lipoxygenase or chelation of Fe3+ is not responsible for the observed activity. Compounds bearing a 10-cinnamoyl group were somewhat less active than their less rigid dihydrocinnamoyl congeners. Many compounds were also potent inhibitors of the growth of HaCaT cells with IC50 values in the submicromolar range. Their activity in this assay was equivalent to that observed with the antipsoriatic anthralin, whereas unspecific cytotoxicity was largely reduced as documented by the activity of lactate dehydrogenase released from cytoplasm of keratinocytes. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80021-x

文献信息

• 10-Hydrocinnamoyl- and 10-cinnamoyl-1,8-dihydroxy-9(10H)-anthracenones as inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth
  作者：Klaus Müller、Hans Reindl、Ingo Gawlik

  DOI：10.1016/s0223-5234(99)80021-x

  日期：1998.12

  A series of 10-hydrocinnamoyl and 10-cinnamoyl-1,8-dihydroxy-9(10H)-anthracenones has been synthesized and evaluated as inhibitors of leukotriene B-4 (LTB4) biosynthesis and as antiproliferative agents. In the hydrocinnamoyl series, compounds with phenolic hydroxyl groups were less potent inhibitors of LTB4 biosynthesis than their non-phenolic analogs, suggesting that a nonspecific redox interaction between the compounds and the active site Fe3+ of 5-lipoxygenase or chelation of Fe3+ is not responsible for the observed activity. Compounds bearing a 10-cinnamoyl group were somewhat less active than their less rigid dihydrocinnamoyl congeners. Many compounds were also potent inhibitors of the growth of HaCaT cells with IC50 values in the submicromolar range. Their activity in this assay was equivalent to that observed with the antipsoriatic anthralin, whereas unspecific cytotoxicity was largely reduced as documented by the activity of lactate dehydrogenase released from cytoplasm of keratinocytes. (C) Elsevier, Paris.