(E)-(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl 3-(2,3-dimethoxyphenyl)acrylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (E)-(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl 3-(2,3-dimethoxyphenyl)acrylate
• 英文别名: (4,5-dihydroxy-9,10-dioxoanthracen-2-yl)methyl (E)-3-(2,3-dimethoxyphenyl)prop-2-enoate
• 化学式: C₂₆H₂₀O₈
• 分子量: 460.44
• InChiKey: IZDBQZFKJYYUGE-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  芦荟大黄素 、 2,3-二甲氧基肉桂酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 (E)-(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl 3-(2,3-dimethoxyphenyl)acrylate
  参考文献：
  名称：

  Isolation of antiplasmodial anthraquinones from Kniphofia ensifolia, and synthesis and structure–activity relationships of related compounds

  摘要：

  Bioassay-guided separation of the South African plant Kniphofia ensifolia for antiplasmodial activity led to the isolation of two new anthraquinones, named kniphofiones A and B (3 and 4), together with three known bioactive anthraquinone monomers (1, 2 and 5), and four known bisanthraquinones (6-9). The structures of the two new compounds were elucidated based on analyses of their 1D and 2D NMR spectra and mass spectrometric data. The dimeric compounds 6 and 7 displayed the strongest antiplasmodial activity among all the isolated compounds, with IC50 values of 0.4 +/- 0.1 and 0.2 +/- 0.1 mu M, respectively. The two new compounds displayed modest activities, with IC50 values of 26 +/- 4 and 9 +/- 1 mu M, respectively. Due to the synthetic accessibility of the new compounds and the increased activity shown by the dimeric compounds, a structure-activity relationship study was conducted. As a result, one analogue of kniphofione B (4), the caffeic acid derivative of aloe-emodin, was found to have the highest activity among all the aloe-emodin derivatives, with an IC50 value of 1.3 +/- 0.2 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.032

文献信息

• Isolation of antiplasmodial anthraquinones from Kniphofia ensifolia, and synthesis and structure–activity relationships of related compounds
  作者：Yumin Dai、Liva Harinantenaina、Jessica D. Bowman、Isabel Osorio Da Fonseca、Peggy J. Brodie、Michael Goetz、Maria B. Cassera、David G.I. Kingston

  DOI：10.1016/j.bmc.2013.11.032

  日期：2014.1

  Bioassay-guided separation of the South African plant Kniphofia ensifolia for antiplasmodial activity led to the isolation of two new anthraquinones, named kniphofiones A and B (3 and 4), together with three known bioactive anthraquinone monomers (1, 2 and 5), and four known bisanthraquinones (6-9). The structures of the two new compounds were elucidated based on analyses of their 1D and 2D NMR spectra and mass spectrometric data. The dimeric compounds 6 and 7 displayed the strongest antiplasmodial activity among all the isolated compounds, with IC50 values of 0.4 +/- 0.1 and 0.2 +/- 0.1 mu M, respectively. The two new compounds displayed modest activities, with IC50 values of 26 +/- 4 and 9 +/- 1 mu M, respectively. Due to the synthetic accessibility of the new compounds and the increased activity shown by the dimeric compounds, a structure-activity relationship study was conducted. As a result, one analogue of kniphofione B (4), the caffeic acid derivative of aloe-emodin, was found to have the highest activity among all the aloe-emodin derivatives, with an IC50 value of 1.3 +/- 0.2 mu M. (C) 2013 Elsevier Ltd. All rights reserved.