(E)-6-methoxy-2-oxo-2H-chromen-7-yl 3-(3,4,5-trimethoxyphenyl)acrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-6-methoxy-2-oxo-2H-chromen-7-yl 3-(3,4,5-trimethoxyphenyl)acrylate
• 英文别名: Antitumor agent-93；(6-methoxy-2-oxochromen-7-yl) (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
• 化学式: C₂₂H₂₀O₈
• 分子量: 412.396
• InChiKey: JBYFBRZZBFDEAS-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-hydroxy-6-methoxy-2-oxo-2H-chromene-3-carboxylic acid 在 吡啶 作用下， 反应 2.0h， 生成 (E)-6-methoxy-2-oxo-2H-chromen-7-yl 3-(3,4,5-trimethoxyphenyl)acrylate
  参考文献：
  名称：

  Synthesis, in vitro and in vivo antitumor activity of scopoletin-cinnamic acid hybrids

  摘要：

  A series of hybrids of scopoletin and substituted cinnamic acid were designed, synthesized and evaluated in vitro and in vivo against five human tumor cell lines [MCF-7, MDA-MB-231, A549, HCT-116, and HeLa] with doxorubicin as the positive control. Compounds 17a, 17b, 17c and 17g exhibited potent cytotoxic activity. Especially, compound 17b displayed broad spectrum activity with IC50 values ranging from 0.249 mu M to 0.684 mu M. Moreover, in a preliminary pharmacological study, 17b not only remarkably induced cellular apoptosis, but also clearly induced A549 cells cycle arrest at S phase. In vivo study showed that 17b significantly suppressed tumor growth in a dose-dependent manner without causing the loss of the mean body weight of mice, which was superior to doxorubicin. These preliminary results indicate that 17b is an optimal anti-cancer leading compound and merit further structural modification. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.040

文献信息

• Synthesis, in vitro and in vivo antitumor activity of scopoletin-cinnamic acid hybrids
  作者：Linhu Li、Peng Zhao、Jinglin Hu、Jinhong Liu、Yan Liu、Zhiqiang Wang、Yufeng Xia、Yue Dai、Li Chen

  DOI：10.1016/j.ejmech.2015.01.040

  日期：2015.3

  A series of hybrids of scopoletin and substituted cinnamic acid were designed, synthesized and evaluated in vitro and in vivo against five human tumor cell lines [MCF-7, MDA-MB-231, A549, HCT-116, and HeLa] with doxorubicin as the positive control. Compounds 17a, 17b, 17c and 17g exhibited potent cytotoxic activity. Especially, compound 17b displayed broad spectrum activity with IC50 values ranging from 0.249 mu M to 0.684 mu M. Moreover, in a preliminary pharmacological study, 17b not only remarkably induced cellular apoptosis, but also clearly induced A549 cells cycle arrest at S phase. In vivo study showed that 17b significantly suppressed tumor growth in a dose-dependent manner without causing the loss of the mean body weight of mice, which was superior to doxorubicin. These preliminary results indicate that 17b is an optimal anti-cancer leading compound and merit further structural modification. (C) 2015 Elsevier Masson SAS. All rights reserved.