Butyl-1,8-dihydroxy-9-(10H)anthracenone

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Butyl-1,8-dihydroxy-9-(10H)anthracenone
• 英文别名: 2-butyl-1,8-dihydroxy-10H-anthracen-9-one
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: DLRVAHCNVVWDMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  2-n-butyl-1-hydroxy-8-methoxy-9,10-anthraquinone 在 盐酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 以82%的产率得到Butyl-1,8-dihydroxy-9-(10H)anthracenone
  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

文献信息

• Substituted 1,8-dihydroxy-9-(10H)anthracenones
  申请人：Boehringer Ingelheim GmbH

  公开号：US04327114A1

  公开（公告）日：1982-04-27

  Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical to or different from each other, are each hydrogen, halogen, branched alkyl of 3 to 12 carbon atoms or cycloalkyl of 3 to 12 carbon atoms, provided, however, that at least one of R.sub.1 to R.sub.4 is other than hydrogen; the compounds are useful as dermatologics for the treatment of psoriasis, dandruff, ichthyosis and hyperkeratotic skin conditions.

  式##STR1##的化合物，其中R.sub.1、R.sub.2、R.sub.3和R.sub.4，它们可以相同也可以不同，分别是氢、卤素、3到12个碳原子的支链烷基或3到12个碳原子的环烷基，但至少R.sub.1到R.sub.4中的一个不是氢；这些化合物可用作治疗银屑病、头皮屑、鱼鳞病和过度角化皮肤病症的皮肤病药物。
• US4327114A
  申请人：——

  公开号：US4327114A

  公开（公告）日：1982-04-27