1,8-dihydroxy-10-[4-(4-methoxyphenyl)butanoyl]-10H-anthracen-9-one

• 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-(4-methoxyphenyl)butanoyl]-10H-anthracen-9-one
• 化学式: C₂₅H₂₂O₅
• 分子量: 402.447
• InChiKey: SJVTVWQYWFIYHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  地蒽酚 、 4-(4-甲氧基苯基)丁基氯 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以24%的产率得到1,8-dihydroxy-10-[4-(4-methoxyphenyl)butanoyl]-10H-anthracen-9-one
  参考文献：
  名称：

  10-Phenylbutyryl-substituted anthracenones as inhibitors of keratinocyte growth and LTB4 biosynthesis

  摘要：

  A recent observation that phenylbutyryl anthracenone 2, an analogue of the antipsoriatic anthralin, is a potent inhibitor of leukotriene B-4 (LTB4) biosynthesis has prompted a search of other anthracenones with improved antiproliferative activity. In that direction, a limited number of analogues related to 2 have been prepared and evaluated in the HaCaT keratinocytes proliferation and in the polymorphonuclear leukocyte LTB4 assay. The 4-methoxy analogue 2a and the side chain methylated 21 retain the full inhibitory activity of 1 against LTB4 biosynthesis while their antiproliferative activity is markedly enhanced and comparable to that of the antipsoriatic anthralin. In contrast to anthralin, cytotoxic effects against cell membranes are strongly reduced as documented by the LDH activity released from cytoplasm of keratinocytes. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01212-0

文献信息

• 10-Phenylbutyryl-substituted anthracenones as inhibitors of keratinocyte growth and LTB4 biosynthesis
  作者：Klaus Müller、Klaus Breu、Hans Reindl

  DOI：10.1016/s0223-5234(01)01212-0

  日期：2001.2

  A recent observation that phenylbutyryl anthracenone 2, an analogue of the antipsoriatic anthralin, is a potent inhibitor of leukotriene B-4 (LTB4) biosynthesis has prompted a search of other anthracenones with improved antiproliferative activity. In that direction, a limited number of analogues related to 2 have been prepared and evaluated in the HaCaT keratinocytes proliferation and in the polymorphonuclear leukocyte LTB4 assay. The 4-methoxy analogue 2a and the side chain methylated 21 retain the full inhibitory activity of 1 against LTB4 biosynthesis while their antiproliferative activity is markedly enhanced and comparable to that of the antipsoriatic anthralin. In contrast to anthralin, cytotoxic effects against cell membranes are strongly reduced as documented by the LDH activity released from cytoplasm of keratinocytes. (C) 2001 Editions scientifiques et medicales Elsevier SAS.