2-(E)-[2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,8-dimethoxy-9,10-anthracenedione | 462628-83-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(E)-[2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,8-dimethoxy-9,10-anthracenedione
• 英文别名: 2-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,8-dimethoxyanthracene-9,10-dione
• CAS: 462628-83-7
• 化学式: C₂₅H₂₀O₆
• 分子量: 416.43
• InChiKey: QEQHHQWCTJAWSV-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(E)-[2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,8-dimethoxy-9,10-anthracenedione 在 palladium on activated charcoal 盐酸 、 氢气 、 tin(ll) chloride 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 15.0h， 生成 1,8-dihydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-10H-anthracen-9-one
  参考文献：
  名称：

  2-Arylalkyl-substituted anthracenones as inhibitors of 12-lipoxygenase enzymes. 2. Structure–activity relationships of the linker chain

  摘要：

  A series of 2-arylalkyl-substituted anthracenones were tested as inhibitors of three types of 12-lipoxygenase isoforms in epidermal homogenate of mice, bovine platelets and porcine leukocytes. Their inhibitory activities were compared with those to inhibit the 5-lipoxygenase enzyme in bovine leukocytes. The compounds were synthesised by Marschalk, Wittig or Horner-Emmons reaction at the anthracenedione stage and then reduced to the anthracenones. Structure-activity relationship for the chain linking the anthracenone nucleus and the phenyl ring terminus was investigated. The 2-phenylethyl analogues were among the most potent inhibitors, and 3,4-dimethoxy-substituted 10f was identified as a selective inhibitor of the 12-LO enzymes over 5-LO. Selectivity for 12-LO isoforms was observed with an increase in the overall lipophilicity of the inhibitors. However, none of the linker chains of the 2-substituted anthracenones provided inhibitors that were able to discriminate between the 12-LO isoforms. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(01)01291-0
• 作为产物：
  描述：

  2-bromomethyl-1,8-dimethoxy-9,10-anthracenedione 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 1.08h， 生成 2-(E)-[2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1,8-dimethoxy-9,10-anthracenedione
  参考文献：
  名称：

  2-Arylalkyl-substituted anthracenones as inhibitors of 12-lipoxygenase enzymes. 2. Structure–activity relationships of the linker chain

  摘要：

  A series of 2-arylalkyl-substituted anthracenones were tested as inhibitors of three types of 12-lipoxygenase isoforms in epidermal homogenate of mice, bovine platelets and porcine leukocytes. Their inhibitory activities were compared with those to inhibit the 5-lipoxygenase enzyme in bovine leukocytes. The compounds were synthesised by Marschalk, Wittig or Horner-Emmons reaction at the anthracenedione stage and then reduced to the anthracenones. Structure-activity relationship for the chain linking the anthracenone nucleus and the phenyl ring terminus was investigated. The 2-phenylethyl analogues were among the most potent inhibitors, and 3,4-dimethoxy-substituted 10f was identified as a selective inhibitor of the 12-LO enzymes over 5-LO. Selectivity for 12-LO isoforms was observed with an increase in the overall lipophilicity of the inhibitors. However, none of the linker chains of the 2-substituted anthracenones provided inhibitors that were able to discriminate between the 12-LO isoforms. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(01)01291-0

文献信息

• 2-Arylalkyl-substituted anthracenones as inhibitors of 12-lipoxygenase enzymes. 2. Structure–activity relationships of the linker chain
  作者：Klaus Müller、Reinhold Altmann、Helge Prinz

  DOI：10.1016/s0223-5234(01)01291-0

  日期：2002.1

  A series of 2-arylalkyl-substituted anthracenones were tested as inhibitors of three types of 12-lipoxygenase isoforms in epidermal homogenate of mice, bovine platelets and porcine leukocytes. Their inhibitory activities were compared with those to inhibit the 5-lipoxygenase enzyme in bovine leukocytes. The compounds were synthesised by Marschalk, Wittig or Horner-Emmons reaction at the anthracenedione stage and then reduced to the anthracenones. Structure-activity relationship for the chain linking the anthracenone nucleus and the phenyl ring terminus was investigated. The 2-phenylethyl analogues were among the most potent inhibitors, and 3,4-dimethoxy-substituted 10f was identified as a selective inhibitor of the 12-LO enzymes over 5-LO. Selectivity for 12-LO isoforms was observed with an increase in the overall lipophilicity of the inhibitors. However, none of the linker chains of the 2-substituted anthracenones provided inhibitors that were able to discriminate between the 12-LO isoforms. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.