2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)acetic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)acetic acid
• 英文别名: 2-[2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxochromen-3-yl]oxyacetic acid
• 化学式: C₂₁H₂₀O₉
• 分子量: 416.384
• InChiKey: ZSKWAFMYUPACTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  113.66
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)acetic acid 、 1-(2-hydroxy-phenyl)-5-(4-methoxy-phenyl)-penta-1,4-dien-3-one 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 2-((1E,4E)-5-(4-methoxyphenyl)-3-oxopenta-1,4-dien-1-yl)phenyl-2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)acetate
  参考文献：
  名称：

  Design, synthesis, and antiviral activity of novel rutin derivatives containing 1, 4-pentadien-3-one moiety

  摘要：

  Rutin (compound 5) and some compounds (compounds 1-4 and 6) were isolated from Artemisia princeps Pamp (A. prirtceps Pamp.) and a series of novel rutin derivatives containing 1,4-pentadien-3-one moiety were designed and synthesized. The target compounds were characterized by proton nuclear magnetic resonance spectroscopy (H-1 NMR), carbon nuclear magnetic resonance spectroscopy (C-13 NMR), and ESI-MS. Bioassay results indicated that some of the compounds showed good to excellent antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) at 500 mu g/mL in vivo. The 50% effective concentrations (EC50) of the compound 7r against CMV was 394.78 mu g/mL, which was better than that of Ningnanmycin (432.22 mu g/mL). These results indicated that novel rutin derivatives containing 1,4-pentadien-3-one moiety can effectively control CMV. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.017
• 作为产物：
  描述：

  芦丁 在 盐酸 、 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 72.5h， 生成 2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)acetic acid
  参考文献：
  名称：

  Design, synthesis, and antiviral activity of novel rutin derivatives containing 1, 4-pentadien-3-one moiety

  摘要：

  Rutin (compound 5) and some compounds (compounds 1-4 and 6) were isolated from Artemisia princeps Pamp (A. prirtceps Pamp.) and a series of novel rutin derivatives containing 1,4-pentadien-3-one moiety were designed and synthesized. The target compounds were characterized by proton nuclear magnetic resonance spectroscopy (H-1 NMR), carbon nuclear magnetic resonance spectroscopy (C-13 NMR), and ESI-MS. Bioassay results indicated that some of the compounds showed good to excellent antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) at 500 mu g/mL in vivo. The 50% effective concentrations (EC50) of the compound 7r against CMV was 394.78 mu g/mL, which was better than that of Ningnanmycin (432.22 mu g/mL). These results indicated that novel rutin derivatives containing 1,4-pentadien-3-one moiety can effectively control CMV. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.017