7-(benzyloxy)-5-hydroxy-6-(2-hydroxyethoxy)-2-phenyl-4H-chromen-4-one | 1357354-95-0

• 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: 7-(benzyloxy)-5-hydroxy-6-(2-hydroxyethoxy)-2-phenyl-4H-chromen-4-one
• 英文别名: 7-(benzyloxy)-5-hydroxy-6-(2-hydroxyethoxy)-2-phenyl-4H-1-benzopyran-4-one；5-Hydroxy-6-(2-hydroxyethoxy)-2-phenyl-7-phenylmethoxychromen-4-one；5-hydroxy-6-(2-hydroxyethoxy)-2-phenyl-7-phenylmethoxychromen-4-one
• CAS: 1357354-95-0
• 化学式: C₂₄H₂₀O₆
• 分子量: 404.419
• InChiKey: CXULYWNSIGRNFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-(benzyloxy)-5-hydroxy-6-(2-hydroxyethoxy)-2-phenyl-4H-chromen-4-one 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 5,7-dihydroxy-6-(2-hydroxyethoxy)-2-phenyl-4H-chromen-4-one
  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
• 作为产物：
  描述：

  黄芩苷 在 盐酸 、 碳酸氢钠 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 56.0h， 生成 7-(benzyloxy)-5-hydroxy-6-(2-hydroxyethoxy)-2-phenyl-4H-chromen-4-one
  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

• Synthesis of Ring A-Modified Baicalein Derivatives
  作者：Jun-Fei Wang、Ning Ding、Wei Zhang、Peng Wang、Ying-Xia Li

  DOI：10.1002/hlca.201100162

  日期：2011.12

  Baicalein, an important active constituent of the traditional Chinese herb Scutellaria baicalensis, exhibited antitumor activity and inhibitory activity against P‐gp 170. The syntheses of 25 baicalein derivatives, 2–26 (Table), are described here (Scheme 1). These compounds were systematically modified with O‐alkylation and O‐acylation at HOC(5), HOC(6), and HOC(7), singly or in combination, on

  黄ical素是传统中草药黄cut的重要活性成分，具有抗P-gp 170的抗肿瘤活性和抑制活性。这里描述了25种黄ical素衍生物2 – 26的合成（表1）（方案1）。这些化合物进行了系统的修饰ö烷基化和ö酰化在HO  C（5），HO  C（6），和HO  C（7），单独或组合，在环甲为了评价这样的修改对他们的抑制活性对耐多药的肿瘤细胞系和P-gp的作用的黄芩素170在110的高选择性，高效的烷基化全乙酰化的黄芩素C（7）是关键的区别HO  C（6）和HO 黄芩素的C（7）。
• 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.