2-((5,7-dihydroxy-4-oxo-2-phenyl-4H-chromen-6-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-((5,7-dihydroxy-4-oxo-2-phenyl-4H-chromen-6-yl)oxy)acetic acid
• 英文别名: 2-(5,7-Dihydroxy-4-oxo-2-phenylchromen-6-yl)oxyacetic acid；2-(5,7-dihydroxy-4-oxo-2-phenylchromen-6-yl)oxyacetic acid
• 化学式: C₁₇H₁₂O₇
• 分子量: 328.278
• InChiKey: BLLXCQUOKSAFMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  黄芩苷 在 盐酸 、 aluminum (III) chloride 、 碳酸氢钠 、 potassium carbonate 、 N,N-二甲基苯胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 48.0h， 生成 2-((5,7-dihydroxy-4-oxo-2-phenyl-4H-chromen-6-yl)oxy)acetic acid
  参考文献：
  名称：

  Anti-angiogenic and anticancer effects of baicalein derivatives based on transgenic zebrafish model

  摘要：

  Angiogenesis leads to tumor neovascularization by promoting tumor growth and metastatic spread, therefore, angiogenesis is considered as an attractive target for potential small molecule anticancer drug discovery. Herein, we report the structural modification and biological evaluation of baicalein derivatives, among which compound 42 had potent in vivo anti-angiogenic activity and wide security treatment window in transgenic zebrafish model. Further, 42 exhibited the most potent inhibitory activity on HUVEC proliferation, migration and tube formation in vitro. Moreover, 42 significantly inhibited growth of human lung cancer A549 cells and weak influence on human normal fibroblast L929 cells. The present research demonstrated that the significant anti-angiogenic and anticancer effects, which provided the supportive evidence for 42 could be used as a potential compound of cancer therapy.

  DOI：

  10.1016/j.bmc.2018.07.037

文献信息

• Anti-angiogenic and anticancer effects of baicalein derivatives based on transgenic zebrafish model
  作者：Xueyang Jiang、Junting Zhou、Qinghua Lin、Guiyi Gong、Haopeng Sun、Wenyuan Liu、Qinglong Guo、Feng Feng、Wei Qu

  DOI：10.1016/j.bmc.2018.07.037

  日期：2018.8

  Angiogenesis leads to tumor neovascularization by promoting tumor growth and metastatic spread, therefore, angiogenesis is considered as an attractive target for potential small molecule anticancer drug discovery. Herein, we report the structural modification and biological evaluation of baicalein derivatives, among which compound 42 had potent in vivo anti-angiogenic activity and wide security treatment window in transgenic zebrafish model. Further, 42 exhibited the most potent inhibitory activity on HUVEC proliferation, migration and tube formation in vitro. Moreover, 42 significantly inhibited growth of human lung cancer A549 cells and weak influence on human normal fibroblast L929 cells. The present research demonstrated that the significant anti-angiogenic and anticancer effects, which provided the supportive evidence for 42 could be used as a potential compound of cancer therapy.