2-(3,4-dimethoxyphenyl)-5-methoxybenzo[b]furan | 1257325-92-0

• 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-(3,4-dimethoxyphenyl)-5-methoxybenzo[b]furan
• 英文别名: 2-(3,4-dimethoxyphenyl)-5-methoxybenzofuran；2-(3,4-Dimethoxyphenyl)-5-methoxy-1-benzofuran
• CAS: 1257325-92-0
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: MNUCVQILQWXEPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)-5-methoxybenzo[b]furan 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以88%的产率得到2-(3',4'-dihydroxyphenyl)-5-hydroxybenzo[b]furan
  参考文献：
  名称：

  Design and synthesis of 2-phenylnaphthalenoids and 2-phenylbenzofuranoids as DNA topoisomerase inhibitors and antitumor agents

  摘要：

  Eight 2-phenylnaphthalenoids (2PNs) (3a h) and twenty four 2-phenylbenzofuranoids (2PBF5) (4a-4j, 5a-5j, 6a, 6f-6h) were successfully designed, synthesized and their antiproliferative and in vitro DNA topoisomerase inhibitory activities were evaluated. Nine compounds (four 2PNs and five 2PBFs) showed either Topol or TopoII alpha inhibitory activities. Six compounds (four 2PNs and two 2PBFs) exhibited potent cytotoxicity with IC50 values for 72 h exposure ranging from 0.3 to above 20 mu M against MDA-MB-231, MDA-MB-435, HepG2 and PC3 cell lines. The two 2PBFs displayed comparable and even better antiproliferative as well as TopoII alpha inhibitory activities than 2PNs. Interestingly, the active 2PBFs displayed different mechanisms of TopoII alpha inhibition from that of 2PNs, suggesting that the chromophore scaffold replacement may result in a change of the binding site of inhibitors to TopoII alpha. Furthermore, the mechanisms of antiproliferation on MDA-MB-231 cells indicate that compounds 5a and 5f are promising for further development of anticancer agents. The results of this study reveal that the evolutionary strategy of medicinal chemistry through scaffold hopping is a promising strategy for structure optimization of TopoII alpha inhibitors. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.048
• 作为产物：
  描述：

  2-羟基-5-甲氧基苯甲醛 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium fluoride 、 copper(l) iodide 、 caesium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 10.08h， 生成 2-(3,4-dimethoxyphenyl)-5-methoxybenzo[b]furan
  参考文献：
  名称：

  Design and synthesis of 2-phenylnaphthalenoids and 2-phenylbenzofuranoids as DNA topoisomerase inhibitors and antitumor agents

  摘要：

  Eight 2-phenylnaphthalenoids (2PNs) (3a h) and twenty four 2-phenylbenzofuranoids (2PBF5) (4a-4j, 5a-5j, 6a, 6f-6h) were successfully designed, synthesized and their antiproliferative and in vitro DNA topoisomerase inhibitory activities were evaluated. Nine compounds (four 2PNs and five 2PBFs) showed either Topol or TopoII alpha inhibitory activities. Six compounds (four 2PNs and two 2PBFs) exhibited potent cytotoxicity with IC50 values for 72 h exposure ranging from 0.3 to above 20 mu M against MDA-MB-231, MDA-MB-435, HepG2 and PC3 cell lines. The two 2PBFs displayed comparable and even better antiproliferative as well as TopoII alpha inhibitory activities than 2PNs. Interestingly, the active 2PBFs displayed different mechanisms of TopoII alpha inhibition from that of 2PNs, suggesting that the chromophore scaffold replacement may result in a change of the binding site of inhibitors to TopoII alpha. Furthermore, the mechanisms of antiproliferation on MDA-MB-231 cells indicate that compounds 5a and 5f are promising for further development of anticancer agents. The results of this study reveal that the evolutionary strategy of medicinal chemistry through scaffold hopping is a promising strategy for structure optimization of TopoII alpha inhibitors. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.048

文献信息

• 2-Substituted Benzo[b]furans from (E)-1,2-Dichlorovinyl Ethers and Organoboron Reagents: Scope and Mechanistic Investigations into the One-Pot Suzuki Coupling/Direct Arylation
  作者：Laina M. Geary、Philip G. Hultin

  DOI：10.1002/ejoc.201000787

  日期：2010.10

  phenols, boronic acids or other organoboron reagents, and trichloroethylene. The overall process requires only two synthetic steps, with the key step being a one-pot sequential Suzuki cross-coupling/direct arylation reaction. The method tolerates many useful functional groups and does not require the installation of any other activating functionality. The modular nature of the process permits the rapid

  2-取代的苯并[b]呋喃可以很容易地由简单的苯酚、硼酸或其他有机硼试剂和三氯乙烯组装而成。整个过程只需要两个合成步骤，关键步骤是一锅顺序 Suzuki 交叉偶联/直接芳基化反应。该方法可以容忍许多有用的功能组，并且不需要安装任何其他激活功能。该过程的模块化特性允许使用基本相同的化学物质快速合成许多类似物，在药物开发中具有特殊价值。动力学同位素效应研究的结果和对该过程区域选择性的研究表明，直接芳基化步骤很可能不涉及亲电钯化。