5-O-(ethoxycarbonyl)methyl-7-O-benzoyl chrysin | 1577233-41-0

• 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: 5-O-(ethoxycarbonyl)methyl-7-O-benzoyl chrysin
• 英文别名: [5-(2-Ethoxy-2-oxoethoxy)-4-oxo-2-phenylchromen-7-yl] benzoate；[5-(2-ethoxy-2-oxoethoxy)-4-oxo-2-phenylchromen-7-yl] benzoate
• CAS: 1577233-41-0
• 化学式: C₂₆H₂₀O₇
• 分子量: 444.441
• InChiKey: QLOMWTQNQXXFTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-O-(ethoxycarbonyl)methyl-7-O-benzoyl chrysin 在 甲醇 、 potassium hydroxide 作用下， 反应 2.0h， 以43%的产率得到5-O-carboxymethyl chrysin
  参考文献：
  名称：

  Synthesis and antitumor activity evaluation of chrysin derivatives

  摘要：

  A series of 5,7-disubstituted chrysin, 7-monosubstituted chrysin, 5-monosubstituted chrysin derivatives were synthesized by alkylation, acetylation, benzoylation, carboxymethylation, and evaluated on their antitumor activity of H22 cells in the search for potential antitumor agents. Among them, compound 3 (5,7-diacetyl chrysin) displayed the most potent antitumor activity with IC50 value of 141 mu M. Moreover, there is significant up-regulation of G2 in cell cycle of H22. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.044
• 作为产物：
  描述：

  白杨素 在 吡啶 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 10.0h， 生成 5-O-(ethoxycarbonyl)methyl-7-O-benzoyl chrysin
  参考文献：
  名称：

  Synthesis and antitumor activity evaluation of chrysin derivatives

  摘要：

  A series of 5,7-disubstituted chrysin, 7-monosubstituted chrysin, 5-monosubstituted chrysin derivatives were synthesized by alkylation, acetylation, benzoylation, carboxymethylation, and evaluated on their antitumor activity of H22 cells in the search for potential antitumor agents. Among them, compound 3 (5,7-diacetyl chrysin) displayed the most potent antitumor activity with IC50 value of 141 mu M. Moreover, there is significant up-regulation of G2 in cell cycle of H22. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.044

文献信息

• Synthesis and antitumor activity evaluation of chrysin derivatives
  作者：Zhen-Yuan Zhu、Wan-Xiao Wang、Zhen-qian Wang、Li-Jing Chen、Jing-Yi Zhang、Xiao-cui Liu、Shao-ping Wu、Yong-min Zhang

  DOI：10.1016/j.ejmech.2013.12.044

  日期：2014.3

  A series of 5,7-disubstituted chrysin, 7-monosubstituted chrysin, 5-monosubstituted chrysin derivatives were synthesized by alkylation, acetylation, benzoylation, carboxymethylation, and evaluated on their antitumor activity of H22 cells in the search for potential antitumor agents. Among them, compound 3 (5,7-diacetyl chrysin) displayed the most potent antitumor activity with IC50 value of 141 mu M. Moreover, there is significant up-regulation of G2 in cell cycle of H22. (C) 2014 Elsevier Masson SAS. All rights reserved.