6-phenyl-4-(3,4,5-trimethoxyphenyl)-2H-chromene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 6-phenyl-4-(3,4,5-trimethoxyphenyl)-2H-chromene
• 化学式: C₂₄H₂₂O₄
• 分子量: 374.436
• InChiKey: ZUVBEQREOYUQTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-phenyl-2,3-dihydro-4H-1-benzopyran-4-one 在 1,1'-双(二苯基膦)二茂铁 、 双(乙腈)氯化钯(II) 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.08h， 生成 6-phenyl-4-(3,4,5-trimethoxyphenyl)-2H-chromene
  参考文献：
  名称：

  Rapid synthesis of 4-arylchromenes from ortho-substituted alkynols: A versatile access to restricted isocombretastatin A-4 analogues as antitumor agents

  摘要：

  Potent anticancer 4-arylchromene agents 6, as restricted isoCA-4 analogues, were prepared with excellent yields by a rapid and versatile synthetic pathway. First, in the presence of PTSA in EtOH, a variety of arylalkynols 9 were transformed into substituted 4-chromanones 10 in a one pot procedure which include regioselective arylalkynols hydration, alcohol etherification, MOM-cleavage, and cyclization. Further palladium coupling reactions, using aryl halides and N-tosylhydrazones 11 gave access to a small library of functionalized 4-arylchromenes 6 with good yields. From this series of 4-arylchromenes, we have identified compound 6s which inhibit tubulin assembly at a micromolar level and demonstrate a remarkable nanomolar level of cytotoxicity against four human cancer cell lines. Docking studies showed that isoCA-4 and its restricted chromene analogue 6s adopt a similar positioning in the colchicine binding-site of tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.024