2-(4-chlorophenyl)-3-(2,4-dihydroxyphenyl)-6-hydroxy-benzo[b]furan

• 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: 2-(4-chlorophenyl)-3-(2,4-dihydroxyphenyl)-6-hydroxy-benzo[b]furan
• 英文别名: 4-(2-(4-chlorophenyl)-6-hydroxybenzofuran-3-yl)benzene-1,3-diol；4-[2-(4-Chlorophenyl)-6-hydroxy-1-benzofuran-3-yl]benzene-1,3-diol
• 化学式: C₂₀H₁₃ClO₄
• 分子量: 352.774
• InChiKey: LWVZMWXADHMHDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-(4-chloro-phenyl)-2,2-dihydroxy-ethanone 、 间苯二酚 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以79%的产率得到2-(4-chlorophenyl)-3-(2,4-dihydroxyphenyl)-6-hydroxy-benzo[b]furan
  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

• Investigation on the condensation of α and β ketoaldehydes with hydroxyaromatic compounds
  作者：Naciye Talinli、Bekir Karliga

  DOI：10.1002/jhet.5570410210

  日期：2004.3

  Mechanism of the condensation reactions of methylglyoxal, phenylglyoxal and benzoylacetaldehyde with phenolic compounds have been discussed. It was observed that the reaction mechanisms changed depending on the type of the phenolic and also dicarbonyl compounds. While, methylglyoxal gave the angular methyl derivative of naphthofuraranonaphthofuran with 2-naphthol, phenylglyoxal and its p-chloro and

  讨论了甲基乙二醛，苯乙二醛和苯甲酰乙醛与酚类化合物的缩合反应机理。观察到反应机理根据酚类化合物以及二羰基化合物的类型而改变。而甲基乙二醛使萘呋喃呋喃基萘呋喃与2-萘酚形成角甲基衍生物，苯基乙二醛及其对氯和对甲氧基衍生物形成了苯并[ b ]萘并[ 2,1- f ]氧杂环庚烷-13-。然而，间苯二酚的行为不同，并生成带有苯基乙二醛衍生物的2-苯基-3-（2,4-二羟基）-6-羟基-苯并[ b ]呋喃。2-苯基-4-（2-羟基萘基）-4 H-萘[ b苯甲酰基乙醛与2-萘酚反应制得] pyran，但当相同的羰基化合物时，反应产物为3,9-二羟基-6-苯基-6,12-甲醇-12 H-二苯并[1,3]二氧杂环丁烷与间苯二酚反应。
• 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.