9,10-dihydro-1,8-dimethoxy-9,10-dioxo-2-anthracenecarbaldehyde | 197907-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-dihydro-1,8-dimethoxy-9,10-dioxo-2-anthracenecarbaldehyde
• 英文别名: 1,8-Dimethoxy-9,10-dioxoanthracene-2-carbaldehyde
• CAS: 197907-15-6
• 化学式: C₁₇H₁₂O₅
• 分子量: 296.279
• InChiKey: ZFEOZFVLRHEFMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9,10-dihydro-1,8-dimethoxy-9,10-dioxo-2-anthracenecarbaldehyde 在 盐酸 、 tin(ll) chloride 、 sodium t-butanolate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 2-[2-(3,4-Bis-benzyloxy-phenyl)-ethyl]-1,8-dihydroxy-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 碳酸氢钠 、 二甲基亚砜 作用下， 反应 1.0h， 以60%的产率得到9,10-dihydro-1,8-dimethoxy-9,10-dioxo-2-anthracenecarbaldehyde
  参考文献：
  名称：

  Simple Analogues of Anthralin:  Unusual Specificity of Structure and Antiproliferative Activity

  摘要：

  Fifty-nine simple analogues of the antipsoriatic agent, anthralin, have been prepared by modifying the positions of the 1,8-hydroxyl groups, replacement of the hydroxyl groups, substitution at the oxygen functions, introduction of additional functional groups into various positions of the anthracenone nucleus, or removal of particular structural elements. The compounds were evaluated for their antiproliferative action against human keratinocytes and inhibition of the generation of leukotriene B-4 in polymorphonuclear leukocytes, which may be useful to resolve the proliferative and inflammatory aspects of psoriasis, respectively. Even though many anthracenones were more potent inhibitors of leukotriene biosynthesis than anthralin, none of the compounds was substantially more effective as this drug in suppressing keratinocyte cell growth. There is an absolute requirement for two hydroxyl groups peri to a hydrogen bond acceptor such as a keto or an imino group for high potency. Ln addition to further delineating the nature of the pharmacophore for this class of compounds, also naphthalenedione with a peri hydroxyl group was identified as a pharmacophore with antiproliferative activity against keratinocyte growth.

  DOI：

  10.1021/jm970292n

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.
• Simple Analogues of Anthralin:  Unusual Specificity of Structure and Antiproliferative Activity
  作者：Klaus Müller、Helge Prinz、Ingo Gawlik、Klaus Ziereis、Hsu-Shan Huang

  DOI：10.1021/jm970292n

  日期：1997.11.1

  Fifty-nine simple analogues of the antipsoriatic agent, anthralin, have been prepared by modifying the positions of the 1,8-hydroxyl groups, replacement of the hydroxyl groups, substitution at the oxygen functions, introduction of additional functional groups into various positions of the anthracenone nucleus, or removal of particular structural elements. The compounds were evaluated for their antiproliferative action against human keratinocytes and inhibition of the generation of leukotriene B-4 in polymorphonuclear leukocytes, which may be useful to resolve the proliferative and inflammatory aspects of psoriasis, respectively. Even though many anthracenones were more potent inhibitors of leukotriene biosynthesis than anthralin, none of the compounds was substantially more effective as this drug in suppressing keratinocyte cell growth. There is an absolute requirement for two hydroxyl groups peri to a hydrogen bond acceptor such as a keto or an imino group for high potency. Ln addition to further delineating the nature of the pharmacophore for this class of compounds, also naphthalenedione with a peri hydroxyl group was identified as a pharmacophore with antiproliferative activity against keratinocyte growth.