(E)-16-(3',4',5'-trimethoxybenzylidene)-3-hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (E)-16-(3',4',5'-trimethoxybenzylidene)-3-hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-one
• 英文别名: (8R,9S,13S,14S,16E)-3-hydroxy-2-methoxy-13-methyl-16-[(3,4,5-trimethoxyphenyl)methylidene]-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-one
• 化学式: C₂₉H₃₄O₆
• 分子量: 478.585
• InChiKey: JVJNJCTVHUEEJZ-FSXJNOEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-甲氧基雌二醇 在 吡啶 、 氯化锆(IV) 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (E)-16-(3',4',5'-trimethoxybenzylidene)-3-hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  Discovery of chalcone-modified estradiol analogs as antitumour agents that Inhibit tumour angiogenesis and epithelial to mesenchymal transition

  摘要：

  Angiogenesis plays an essential role in tumourigenesis and tumour progression, and anti-angiogenesis therapies have shown promising antitumour effects in solid tumours. 2-Methoxyestradiol (2ME2), an endogenous metabolite of estradiol, has been regarded as a potential antitumour agent mainly targeting angiogenesis. Here we synthesized a novel series of chalcones based on 2-methoxyestradiol and evaluated their potential activities against tumours. Compound 11e was demonstrated to have potent antiangiogenic activity. Further studies showed that 11e suppressed tumour growth in human breast cancer (MCF-7) xenograft models without obvious side effects. Evaluation of the mechanism revealed that 11e targeted the epithelial to mesenchymal transition (EMT) process in MCF-7 cells and inhibited HUVEC migration and then contributed to hindrance of angiogenesis. Thus, 11e may be a promising antitumour agent with excellent efficacy and low toxicity.

  DOI：

  10.1016/j.ejmech.2019.04.071

文献信息

• Discovery of chalcone-modified estradiol analogs as antitumour agents that Inhibit tumour angiogenesis and epithelial to mesenchymal transition
  作者：Cong Wang、Leilei Li、Dongyang Fu、Tiantian Qin、Yange Ran、Feng Xu、Xinrui Du、Haiying Gao、Shuaijun Sun、Tengjiao Yang、Xueyan Zhang、Junfeng Huo、Wen Zhao、Zhenzhong Zhang、Xiufang Shi

  DOI：10.1016/j.ejmech.2019.04.071

  日期：2019.8

  Angiogenesis plays an essential role in tumourigenesis and tumour progression, and anti-angiogenesis therapies have shown promising antitumour effects in solid tumours. 2-Methoxyestradiol (2ME2), an endogenous metabolite of estradiol, has been regarded as a potential antitumour agent mainly targeting angiogenesis. Here we synthesized a novel series of chalcones based on 2-methoxyestradiol and evaluated their potential activities against tumours. Compound 11e was demonstrated to have potent antiangiogenic activity. Further studies showed that 11e suppressed tumour growth in human breast cancer (MCF-7) xenograft models without obvious side effects. Evaluation of the mechanism revealed that 11e targeted the epithelial to mesenchymal transition (EMT) process in MCF-7 cells and inhibited HUVEC migration and then contributed to hindrance of angiogenesis. Thus, 11e may be a promising antitumour agent with excellent efficacy and low toxicity.