1-hydroxy-8-methoxy-2-(1-oxopropyl)-9,10-anthracenedione | 179737-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-hydroxy-8-methoxy-2-(1-oxopropyl)-9,10-anthracenedione
• 英文别名: 1-hydroxy-8-methoxy-2-propanoylanthracene-9,10-dione
• CAS: 179737-95-2
• 化学式: C₁₈H₁₄O₅
• 分子量: 310.306
• InChiKey: ZAUNJTMWVOGAHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-hydroxy-8-methoxy-2-(1-oxopropyl)-9,10-anthracenedione 在 盐酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 以31%的产率得到1,8-Dihydroxy-2-propionyl-10H-anthracen-9-one
  参考文献：
  名称：

  Simple Analogues of Anthralin:  Unusual Specificity of Structure and Antiproliferative Activity

  摘要：

  Fifty-nine simple analogues of the antipsoriatic agent, anthralin, have been prepared by modifying the positions of the 1,8-hydroxyl groups, replacement of the hydroxyl groups, substitution at the oxygen functions, introduction of additional functional groups into various positions of the anthracenone nucleus, or removal of particular structural elements. The compounds were evaluated for their antiproliferative action against human keratinocytes and inhibition of the generation of leukotriene B-4 in polymorphonuclear leukocytes, which may be useful to resolve the proliferative and inflammatory aspects of psoriasis, respectively. Even though many anthracenones were more potent inhibitors of leukotriene biosynthesis than anthralin, none of the compounds was substantially more effective as this drug in suppressing keratinocyte cell growth. There is an absolute requirement for two hydroxyl groups peri to a hydrogen bond acceptor such as a keto or an imino group for high potency. Ln addition to further delineating the nature of the pharmacophore for this class of compounds, also naphthalenedione with a peri hydroxyl group was identified as a pharmacophore with antiproliferative activity against keratinocyte growth.

  DOI：

  10.1021/jm970292n
• 作为产物：
  描述：

  1-羟基-8-甲氧基-9,10-蒽醌 在 氢氧化钾 、 重铬酸吡啶 、 sodium dithionite 、 air 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.75h， 生成 1-hydroxy-8-methoxy-2-(1-oxopropyl)-9,10-anthracenedione
  参考文献：
  名称：

  2-蒽基乙酸作为 5-脂氧化酶抑制剂

  摘要：

  描述了 2-取代蒽基乙酸 (2-AA) 衍生物的合成。关键步骤是1-羟基-8-甲氧基-蒽二酮与乙醇酸的Marschalk反应。在保护所得的2-蒽基乙酸衍生物后，通过直接烷基化选择性地获得2-单烷基化衍生物。该方法证明非常通用，并允许将各种替代物引入羧基侧链的 2 位。蒽二酮的还原伴随着保护基团的去除进行，并以良好的产率提供最终的 2-AA 产品。初步生物学研究的结果表明，与蒽林相比，5-脂肪氧化酶抑制作用增强。

  DOI：

  10.1002/ardp.19963290507