3-(3,5-difluorophenyl)chroman-4-one | 1529771-72-9

• 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: 3-(3,5-difluorophenyl)chroman-4-one
• 英文别名: 3′,5′-difluoroisoflavanone；3-(3,5-Difluorophenyl)chroman-4-one；3-(3,5-difluorophenyl)-2,3-dihydrochromen-4-one
• CAS: 1529771-72-9
• 化学式: C₁₅H₁₀F₂O₂
• 分子量: 260.24
• InChiKey: DZHXHJPYEOPVKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  水杨醛 、 1-乙炔基-3,5-二氟苯 在 gold(I) cyanide 、 三丁基膦 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以35.8%的产率得到3-(3,5-difluorophenyl)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