4-(4-Benzyloxyphenoxy)Butanesulfonyl Fluoride | 1404225-76-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-Benzyloxyphenoxy)Butanesulfonyl Fluoride
• 英文别名: 4-(4-phenylmethoxyphenoxy)butane-1-sulfonyl fluoride
• CAS: 1404225-76-8
• 化学式: C₁₇H₁₉FO₄S
• 分子量: 338.4
• InChiKey: VFGPUBDBBUDHRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(4-benzyloxyphenoxy)butanesulfonyl chloride 在 氟化铵 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以93%的产率得到4-(4-Benzyloxyphenoxy)Butanesulfonyl Fluoride
  参考文献：
  名称：

  Sulfonyl Fluoride Inhibitors of Fatty Acid Amide Hydrolase

  摘要：

  Sulfonyl fluorides are known to inhibit esterases. Early work, from our laboratory has identified hexadecyl sulfonylfluoride (AM374) as a potent in vitro and in vivo inhibitor of fatty acid amide hydrolase (FAAH). We now report on later generation sulfonyl fluoride analogs that exhibit potent and selective inhibition of FAAH. Using recombinant rat and human FAAH, we show that 5-(4-hydroxyphenyl)pentanesulfonyl fluoride (AM3506) has similar inhibitory activity for both the rat and the human enzyme, while dilution assays and mass spectrometry analysis suggest that the compound is a covalent modifier for FAAH and inhibits its action in an irreversible manner. Our SAR results are highlighted by molecular docking of key analogs.

  DOI：

  10.1021/jm301205j

文献信息

• Sulfonyl Fluoride Inhibitors of Fatty Acid Amide Hydrolase
  作者：Shakiru O. Alapafuja、Spyros P. Nikas、Indu T. Bharathan、Vidyanand G. Shukla、Mahmoud L. Nasr、Anna L. Bowman、Nikolai Zvonok、Jing Li、Xiaomeng Shi、John R. Engen、Alexandros Makriyannis

  DOI：10.1021/jm301205j

  日期：2012.11.26

  Sulfonyl fluorides are known to inhibit esterases. Early work, from our laboratory has identified hexadecyl sulfonylfluoride (AM374) as a potent in vitro and in vivo inhibitor of fatty acid amide hydrolase (FAAH). We now report on later generation sulfonyl fluoride analogs that exhibit potent and selective inhibition of FAAH. Using recombinant rat and human FAAH, we show that 5-(4-hydroxyphenyl)pentanesulfonyl fluoride (AM3506) has similar inhibitory activity for both the rat and the human enzyme, while dilution assays and mass spectrometry analysis suggest that the compound is a covalent modifier for FAAH and inhibits its action in an irreversible manner. Our SAR results are highlighted by molecular docking of key analogs.