4-(4-methoxyphenyl)-6-phenyl-2H-chromene | 1416006-07-9

• 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: 4-(4-methoxyphenyl)-6-phenyl-2H-chromene
• CAS: 1416006-07-9
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: UCDAXIRXADNRIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

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 4-(4-methoxyphenyl)-6-phenyl-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

文献信息

• Gold versus silver catalyzed intramolecular hydroarylation reactions of [(3-arylprop-2-ynyl)oxy]benzene derivatives
  作者：Antonio Arcadi、Federico Blesi、Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani、Fabio Marinelli

  DOI：10.1039/c2ob26763b

  日期：——

  the generality of gold versus silver catalyzed intramolecular hydroarylation reactions of 3-[(3-arylprop-2-ynyl)oxy]benzene derivatives in terms of rings substitution were investigated. Only products deriving from 6-endo cyclization were exclusively formed. The features of substituents had a considerable effect on the reaction outcome in the presence of silver catalysis, whereas gold catalysis revealed

  研究了金与银催化的3-[（（3-芳基丙-2-炔基）氧基]苯衍生物在环取代方面的分子内氢芳基化反应的范围和一般性。仅形成了6-内环化衍生的产品。取代基的特征在存在银催化的情况下对反应结果有相当大的影响，而金催化显示出反应性和选择性的独特混合物，并且是带有电子缺陷的芳烃的起始底物的分子内氢化反应的唯一选择。
• Rapid synthesis of 4-arylchromenes from ortho-substituted alkynols: A versatile access to restricted isocombretastatin A-4 analogues as antitumor agents
  作者：Dolor Renko、Olivier Provot、Evelia Rasolofonjatovo、Jérôme Bignon、Jordi Rodrigo、Joëlle Dubois、Jean-Daniel Brion、Abdallah Hamze、Mouad Alami

  DOI：10.1016/j.ejmech.2014.12.024

  日期：2015.1

  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.