1,8-dihydroxy-2-<<4-(methoxycarbonyl)phenyl>methyl>-9(10H)-anthracenone | 155920-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,8-dihydroxy-2-<<4-(methoxycarbonyl)phenyl>methyl>-9(10H)-anthracenone
• 英文别名: 4-(1,8-Dihydroxy-9-oxo-9,10-dihydro-anthracen-2-ylmethyl)-benzoic acid methyl ester；methyl 4-[(1,8-dihydroxy-9-oxo-10H-anthracen-2-yl)methyl]benzoate
• CAS: 155920-31-3
• 化学式: C₂₃H₁₈O₅
• 分子量: 374.393
• InChiKey: JOUYFNVTNGRAQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,8-dihydroxy-2-<<4-(methoxycarbonyl)phenyl>methyl>-9(10H)-anthracenone 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 以28%的产率得到4-(1,8-Dihydroxy-9-oxo-9,10-dihydro-anthracen-2-ylmethyl)-N-hydroxy-benzamide
  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-羟基-8-甲氧基-9,10-蒽醌 在 盐酸 、 sodium hydroxide 、 sodium dithionite 、 硫酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 反应 27.25h， 生成 1,8-dihydroxy-2-<<4-(methoxycarbonyl)phenyl>methyl>-9(10H)-anthracenone
  参考文献：
  名称：

  Antipsoriatic Anthrones with Modulated Redox Properties. 2. Novel Derivatives of Chrysarobin and Isochrysarobin-Antiproliferative Activity and 5-Lipoxygenase Inhibition

  摘要：

  A novel series of 2- and 3-substituted 1,8-dihydroxy-9(10H)-anthracenones were synthesized and tested for their inhibitory activity against 5-lipoxygenase (5-LO) in bovine polymorphonuclear leukocytes and the growth of human keratinocytes. Structure-activity relationships are discussed with respect to the following redox properties of the compounds: reactivity against 2,2-diphenyl-1-picrylhydrazyl, generation of hydroxyl radicals as measured by deoxyribose degradation, and inhibition of lipid peroxidation in model membranes. Inhibition of cell proliferation seemed to be related to these properties, whereas 5-LO inhibition was not. Within a class of structural analogs the activity against 5-LO, which was markedly improved as compared to that of the antipsoriatic drug anthralin, correlated well with the overall lipophilicity. Even though a number of compounds in this series enhanced oxidative damage to nonlipid molecules such as deoxyribose, their antioxidant properties predominate in membrane lipids. Among the prooxidant compounds were also the most potent antiproliferative agents (IC50 values in the 10(-7) M range).

  DOI：

  10.1021/jm00037a017

文献信息

• US5922891A
  申请人：——

  公开号：US5922891A

  公开（公告）日：1999-07-13