4-(1,8-dihydroxy-9-oxo-10H-anthracen-2-yl)butanoic acid | 85313-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-(1,8-dihydroxy-9-oxo-10H-anthracen-2-yl)butanoic acid
• 英文别名: 4-(1,8-Dihydroxy-9-oxo-9,10-dihydro-anthracen-2-yl)-butyric acid
• CAS: 85313-97-9
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: QPRXYFJEAJPNQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  4-(1,8-dihydroxy-9-oxo-10H-anthracen-2-yl)butanoic acid 在 硫酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 N-hydroxy-N-methyl-4-(9,10-dihydro-1,8-dihydroxy-9-oxo-2-anthracene)butanamide
  参考文献：
  名称：

  Antipsoriatic Anthrones with Modulated Redox Properties. 4. Synthesis and Biological Activity of Novel 9,10-Dihydro-1,8-dihydroxy-9-oxo-2- anthracenecarboxylic and -hydroxamic Acids

  摘要：

  A novel series of carboxylic and hydroxamic acids based on 1,8-dihydroxy-9(10H)-anthracenone were synthesized from 8-hydroxy-1-methoxy-9,10-anthracenedione as the key intermediate and evaluated both in the bovine polymorphonuclear leukocyte 5-lipoxygenase (5-LO) assay and in the HaCaT keratinocyte proliferation assay for their enzyme inhibitory and antiproliferative activity, respectively. The most potent inhibitors in both assays were the N-methylated hydroxamic acids 5d-8d with straight chain alkyl spacers. Incorporation of these structural features on the anthracenone pharmacophore resulted in increased inhibitory activity against 5-LO while the antiproliferative activity was retained. In addition, prooxidant properties as measured by deoxyribose degradation and cytotoxicity as assessed by LDH release were largely reduced as compared with the antipsoriatic anthralin. Contrary to anthralin, antioxidant properties were observed as documented by the reactivity of the novel compounds against free radicals and inhibition of lipid peroxidation in model membranes.

  DOI：

  10.1021/jm9701785
• 作为产物：
  描述：

  1,8-二羟基蒽醌 在 氢氧化钾 、 硫酸 、 potassium carbonate 作用下， 以 吡啶 、 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 37.0h， 生成 4-(1,8-dihydroxy-9-oxo-10H-anthracen-2-yl)butanoic acid
  参考文献：
  名称：

  Studies on the synthesis of 4-(1,8-dioxygenated-9,10-dioxoanthracen(or anthracen)-2-yl)butanoic acid derivatives.

  摘要：

  所述化合物（11-14, 16, 17）预计在合成11-脱氧蒽醌酮中具有重要价值，采用易得的1,8-二羟基蒽-9,10-二酮（千层石（chrysazin））（3）作为原料，通过克莱森重排或马尔沙尔克反应作为关键合成步骤制备而成。

  DOI：

  10.1248/cpb.30.4539

文献信息

• US5922891A
  申请人：——

  公开号：US5922891A

  公开（公告）日：1999-07-13