1-hydroxy-8-methoxy-2-[(4-propoxyphenyl)methyl]-9,10-anthracenedione

• 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-[(4-propoxyphenyl)methyl]-9,10-anthracenedione
• 英文别名: 1-Hydroxy-8-methoxy-2-[(4-propoxyphenyl)methyl]anthracene-9,10-dione
• 化学式: C₂₅H₂₂O₅
• 分子量: 402.447
• InChiKey: AIEJXTYDLPJDNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-hydroxy-8-methoxy-2-[(4-propoxyphenyl)methyl]-9,10-anthracenedione 在 盐酸 、 tin(ll) chloride 作用下， 以 溶剂黄146 为溶剂， 以42%的产率得到1,8-Dihydroxy-2-(4-propoxy-benzyl)-10H-anthracen-9-one
  参考文献：
  名称：

  2-Arylalkyl-substituted anthracenones as inhibitors of 12-lipoxygenase enzymes. 1. Structure–activity relationships of the terminal aryl ring

  摘要：

  A series of 2-arylmethyl-substituted anthracenones were synthesized and tested as inhibitors of three types of 12-lipoxygenase isoforms in epidermal homogenate of mice, bovine platelets and porcine leucocytes. Their inhibitory activities were compared with those to inhibit the 5-lipoxygenase enzyme in bovine leucocytes. Structure-activity relationships are described with particular emphasis on modifications of the terminal aryl nucleuS. The ability of the compounds to selectively inhibit the 12-lipoxygenase enzymes was dependent on a high overall lipophilicity of the inhibitor, whereas compounds with decreased lipophilicity were also inhibitors of the 5-LO enzyme. Among the more lipophilic inhibitors, the unsubstituted 2-phenylmethyl analogue 6a as well as the carboxylic acid ester 6q ap eared to be selective inhibitors of platelet-type 12-LO isoform. (C) 2001 Editions scientifiques et medicales Elsevier SAS

  DOI：

  10.1016/s0223-5234(01)01248-x
• 作为产物：
  描述：

  1-羟基-8-甲氧基-9,10-蒽醌 、 4-丙氧基苯甲醛 在 sodium hydroxide 、 sodium dithionite 作用下， 以 水 为溶剂， 反应 14.25h， 以8%的产率得到1-hydroxy-8-methoxy-2-[(4-propoxyphenyl)methyl]-9,10-anthracenedione
  参考文献：
  名称：

  2-Arylalkyl-substituted anthracenones as inhibitors of 12-lipoxygenase enzymes. 1. Structure–activity relationships of the terminal aryl ring

  摘要：

  A series of 2-arylmethyl-substituted anthracenones were synthesized and tested as inhibitors of three types of 12-lipoxygenase isoforms in epidermal homogenate of mice, bovine platelets and porcine leucocytes. Their inhibitory activities were compared with those to inhibit the 5-lipoxygenase enzyme in bovine leucocytes. Structure-activity relationships are described with particular emphasis on modifications of the terminal aryl nucleuS. The ability of the compounds to selectively inhibit the 12-lipoxygenase enzymes was dependent on a high overall lipophilicity of the inhibitor, whereas compounds with decreased lipophilicity were also inhibitors of the 5-LO enzyme. Among the more lipophilic inhibitors, the unsubstituted 2-phenylmethyl analogue 6a as well as the carboxylic acid ester 6q ap eared to be selective inhibitors of platelet-type 12-LO isoform. (C) 2001 Editions scientifiques et medicales Elsevier SAS

  DOI：

  10.1016/s0223-5234(01)01248-x

文献信息

• 2-Arylalkyl-substituted anthracenones as inhibitors of 12-lipoxygenase enzymes. 1. Structure–activity relationships of the terminal aryl ring
  作者：K Müller

  DOI：10.1016/s0223-5234(01)01248-x

  日期：2001.6

  A series of 2-arylmethyl-substituted anthracenones were synthesized and tested as inhibitors of three types of 12-lipoxygenase isoforms in epidermal homogenate of mice, bovine platelets and porcine leucocytes. Their inhibitory activities were compared with those to inhibit the 5-lipoxygenase enzyme in bovine leucocytes. Structure-activity relationships are described with particular emphasis on modifications of the terminal aryl nucleuS. The ability of the compounds to selectively inhibit the 12-lipoxygenase enzymes was dependent on a high overall lipophilicity of the inhibitor, whereas compounds with decreased lipophilicity were also inhibitors of the 5-LO enzyme. Among the more lipophilic inhibitors, the unsubstituted 2-phenylmethyl analogue 6a as well as the carboxylic acid ester 6q ap eared to be selective inhibitors of platelet-type 12-LO isoform. (C) 2001 Editions scientifiques et medicales Elsevier SAS