4-(6-hydroxy-2-(m-tolyl)benzofuran-3-yl)benzene-1,3-diol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 4-(6-hydroxy-2-(m-tolyl)benzofuran-3-yl)benzene-1,3-diol
• 英文别名: 4-[6-Hydroxy-2-(3-methylphenyl)-1-benzofuran-3-yl]benzene-1,3-diol；4-[6-hydroxy-2-(3-methylphenyl)-1-benzofuran-3-yl]benzene-1,3-diol
• 化学式: C₂₁H₁₆O₄
• 分子量: 332.356
• InChiKey: BMJISNHGQRFLHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  73.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3'-甲基苯乙酮 在 selenium(IV) oxide 、 水 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 25.0h， 生成 4-(6-hydroxy-2-(m-tolyl)benzofuran-3-yl)benzene-1,3-diol
  参考文献：
  名称：

  Synthesis and antitumor evaluation of 2,3-diarylbenzofuran derivatives on HeLa cells

  摘要：

  2,2-Dihydroxyarylethanones, readily prepared from the commercially available aromatic ethyl ketones, were reacted with resorcinol, 3-methoxyphenol or 2-methoxyphenol in multi steps one-pot manner promoted by trifluoroacetic acid to furnish the 2,3-diarylbenzofuran derivatives in 22-95% yield. Sixteen targeted compounds were synthesized and characterized by H-1 NMR, C-13 NMR and HRMS. MIT assay indicated that most compounds possessed effectively inhibitory activities against the proliferation of HeLa cell. Among them, 4f had the highest inhibitory activities, with the IC50 being 13.40 +/- 2.04 mu mol/L. Cell cycle analysis, Annexin V-FITC/propidium iodide dual staining assay and western blotting analysis revealed that 4f inhibited the proliferation of Hela cell through apoptosis induction in a dose-dependent manner via obviously up-regulated the levels of Bak and Bim, while striking down regulated the level of Bcl-2 and BcI-xL protein. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.03.010

文献信息

• Synthesis and antitumor evaluation of 2,3-diarylbenzofuran derivatives on HeLa cells
  作者：Guo-Xue He、Jing-Mei Yuan、Hai-Miao Zhu、Kai Wei、Ling-Yun Wang、Shi-Lin Kong、Dong-Liang Mo、Cheng-Xue Pan、Gui-Fa Su

  DOI：10.1016/j.bmcl.2017.03.010

  日期：2017.4

  2,2-Dihydroxyarylethanones, readily prepared from the commercially available aromatic ethyl ketones, were reacted with resorcinol, 3-methoxyphenol or 2-methoxyphenol in multi steps one-pot manner promoted by trifluoroacetic acid to furnish the 2,3-diarylbenzofuran derivatives in 22-95% yield. Sixteen targeted compounds were synthesized and characterized by H-1 NMR, C-13 NMR and HRMS. MIT assay indicated that most compounds possessed effectively inhibitory activities against the proliferation of HeLa cell. Among them, 4f had the highest inhibitory activities, with the IC50 being 13.40 +/- 2.04 mu mol/L. Cell cycle analysis, Annexin V-FITC/propidium iodide dual staining assay and western blotting analysis revealed that 4f inhibited the proliferation of Hela cell through apoptosis induction in a dose-dependent manner via obviously up-regulated the levels of Bak and Bim, while striking down regulated the level of Bcl-2 and BcI-xL protein. (C) 2017 Elsevier Ltd. All rights reserved.