6-phenylhexane-1-sulfonyl chloride | 1202760-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-phenylhexane-1-sulfonyl chloride
• 英文别名: 6-Phenylhexane-1-sulfonyl chloride
• CAS: 1202760-70-0
• 化学式: C₁₂H₁₇ClO₂S
• 分子量: 260.785
• InChiKey: GNUOJNWRTQKQOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-phenylhexane-1-sulfonyl chloride 在 氟化铵 作用下， 以 丙酮 为溶剂， 以93%的产率得到6-phenylhexane-1-sulfonyl 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
• 作为产物：
  描述：

  (6-iodohexyl)benzene 在 叔丁基锂 、 磺酰氯 作用下， 以 乙醚 、 正己烷 、 正戊烷 为溶剂， 反应 1.17h， 以22%的产率得到6-phenylhexane-1-sulfonyl chloride
  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

• Microwave-assisted synthesis of sodium sulfonates precursors of sulfonyl chlorides and fluorides
  作者：Shakiru O. Alapafuja、Spyros P. Nikas、Vidyanand G. Shukla、Ioannis Papanastasiou、Alexandros Makriyannis

  DOI：10.1016/j.tetlet.2009.09.167

  日期：2009.12

  We describe the use of a microwave reaction for the conversion of various bromides to sodium sulfonates that have been further elaborated to sulfonyl chlorides. This new approach leads to much improved yields and shorter reaction times. Representative sulfonyl chlorides serve as precursors for the respective sulfonyl fluorides that are potent inhibitors of the fatty acid amide hydrolase. (C) 2009 Elsevier Ltd. All rights reserved.
• US7253194B2
  申请人：——

  公开号：US7253194B2

  公开（公告）日：2007-08-07
• 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.