6-methoxy-3-(4-phenoxyphenyl)chroman-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 6-methoxy-3-(4-phenoxyphenyl)chroman-4-one
• 化学式: C₂₂H₁₈O₄
• 分子量: 346.383
• InChiKey: LRGCREBDJRGHSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-羟基-5-甲氧基苯甲醛 、 4-苯氧基苯乙炔 在 gold(I) cyanide 、 三丁基膦 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以36.3%的产率得到6-methoxy-3-(4-phenoxyphenyl)chroman-4-one
  参考文献：
  名称：

  Investigation of fluorinated and bifunctionalized 3-phenylchroman-4-one (isoflavanone) aromatase inhibitors

  摘要：

  Fluorinated isoflavanones and bifunctionalized isoflavanones were synthesized through a one-step gold(I)-catalyzed annulation reaction. These compounds were evaluated for their in vitro inhibitory activities against aromatase in a fluorescence-based enzymatic assay. Selected compounds were tested for their anti-proliferative effects on human breast cancer cell line MCF-7. Compounds 6-methoxy-3-(pyridin-3-yl)chroman-4-one (3c) and 6-fluoro-3-(pyridin-3-yl)chroman-4-one (3e) were identified as the most potent aromatase inhibitors with IC50 values of 2.5 mu M and 0.8 mu M. Therefore, these compounds have great potential for the development of pharmaceutical agents against breast cancer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.045

文献信息

• Investigation of fluorinated and bifunctionalized 3-phenylchroman-4-one (isoflavanone) aromatase inhibitors
  作者：Erica Amato、Tony Bankemper、Rebecca Kidney、Thuy Do、Alma Onate、Fathima Shazna Thowfeik、Edward J. Merino、Stefan Paula、Lili Ma

  DOI：10.1016/j.bmc.2013.11.045

  日期：2014.1

  Fluorinated isoflavanones and bifunctionalized isoflavanones were synthesized through a one-step gold(I)-catalyzed annulation reaction. These compounds were evaluated for their in vitro inhibitory activities against aromatase in a fluorescence-based enzymatic assay. Selected compounds were tested for their anti-proliferative effects on human breast cancer cell line MCF-7. Compounds 6-methoxy-3-(pyridin-3-yl)chroman-4-one (3c) and 6-fluoro-3-(pyridin-3-yl)chroman-4-one (3e) were identified as the most potent aromatase inhibitors with IC50 values of 2.5 mu M and 0.8 mu M. Therefore, these compounds have great potential for the development of pharmaceutical agents against breast cancer. (C) 2013 Elsevier Ltd. All rights reserved.