3-(3,4-difluorophenyl)coumarin-7-O-sulfamate

• 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-(3,4-difluorophenyl)coumarin-7-O-sulfamate
• 英文别名: 3-(3,4-Difluorophenyl)-2-oxo-2h-chromen-7-yl sulfamate；[3-(3,4-difluorophenyl)-2-oxochromen-7-yl] sulfamate
• 化学式: C₁₅H₉F₂NO₅S
• 分子量: 353.303
• InChiKey: DOIJURNENMDCBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,4-二氟苯乙酸 在 氯化亚砜 、 N,N-二甲基乙酰胺 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.5h， 生成 3-(3,4-difluorophenyl)coumarin-7-O-sulfamate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Fluorinated 3‐Phenylcoumarin‐7‐ O ‐Sulfamate Derivatives as Steroid Sulfatase Inhibitors

  摘要：

  In the present work, we report the initial results of our study on a series of 3‐phenylcoumarin sulfamate‐based compounds containing C‐F bonds as novel inhibitors of steroid sulfatase. The new compounds are potent steroid sulfatase inhibitors, possessing more than 10 times higher inhibitory potency than coumarin‐7‐O‐sulfamate. In the course of our investigation, compounds 2b and 2c demonstrated the highest inhibitory effect on the enzymatic steroid sulfatase assay; both had IC50 values of 0.27 μm (the IC50 value of coumarin‐7‐O‐sulfamate is 3.5 μm, used as a reference).

  DOI：

  10.1111/cbdd.12652

文献信息

• Synthesis and Biological Evaluation of Fluorinated 3‐Phenylcoumarin‐7‐ <i>O</i> ‐Sulfamate Derivatives as Steroid Sulfatase Inhibitors
  作者：Sebastian Demkowicz、Mateusz Daśko、Witold Kozak、Katarzyna Krawczyk、Dariusz Witt、Maciej Masłyk、Konrad Kubiński、Janusz Rachon

  DOI：10.1111/cbdd.12652

  日期：2016.2

  In the present work, we report the initial results of our study on a series of 3‐phenylcoumarin sulfamate‐based compounds containing C‐F bonds as novel inhibitors of steroid sulfatase. The new compounds are potent steroid sulfatase inhibitors, possessing more than 10 times higher inhibitory potency than coumarin‐7‐O‐sulfamate. In the course of our investigation, compounds 2b and 2c demonstrated the highest inhibitory effect on the enzymatic steroid sulfatase assay; both had IC50 values of 0.27 μm (the IC50 value of coumarin‐7‐O‐sulfamate is 3.5 μm, used as a reference).