4-(1,8-Dihydroxy-9-oxo-9,10-dihydro-anthracene-2-carbonyl)-benzoic acid methyl ester | 186394-59-2

• 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-9,10-dihydro-anthracene-2-carbonyl)-benzoic acid methyl ester
• 英文别名: methyl 4-(1,8-dihydroxy-9-oxo-10H-anthracene-2-carbonyl)benzoate
• CAS: 186394-59-2
• 化学式: C₂₃H₁₆O₆
• 分子量: 388.376
• InChiKey: XCJIWWFRCQOJJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-甲基羟胺盐酸盐 、 4-(1,8-Dihydroxy-9-oxo-9,10-dihydro-anthracene-2-carbonyl)-benzoic acid methyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以36%的产率得到4-(1,8-Dihydroxy-9-oxo-9,10-dihydro-anthracene-2-carbonyl)-N-hydroxy-N-methyl-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：

  4-[(9,10-dihydro-9,10-dioxo-1-hydroxy-8-methoxy-2-anthracenyl)carbonyl]benzonitrile 在 盐酸 、 硫酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 反应 78.0h， 生成 4-(1,8-Dihydroxy-9-oxo-9,10-dihydro-anthracene-2-carbonyl)-benzoic acid methyl ester
  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

文献信息

• 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
  作者：Klaus Müller、Helge Prinz

  DOI：10.1021/jm9701785

  日期：1997.8.1

  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.