6-phenylhexane-1-sulfonyl fluoride | 1404225-74-6

• 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 fluoride
• 英文别名: 6-Phenylhexane-1-sulfonyl fluoride
• CAS: 1404225-74-6
• 化学式: C₁₂H₁₇FO₂S
• 分子量: 244.33
• InChiKey: UMHRRMYEVADXPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  3

反应信息

• 作为产物：
  描述：

  苯已醇 在 咪唑 、 氟化铵 、 碘 、 叔丁基锂 、 三苯基膦 作用下， 以 乙醚 、 正己烷 、 丙酮 、 乙腈 、 正戊烷 为溶剂， 反应 1.17h， 生成 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

文献信息

• An Easy, General and Practical Method for the Construction of Alkyl Sulfonyl Fluorides
  作者：Xu Zhang、Wan‐Yin Fang、Ravindar Lekkala、Wenjian Tang、Hua‐Li Qin

  DOI：10.1002/adsc.202000515

  日期：2020.8.19

  and 3° alkyl iodides to ethenesulfonyl fluoride, employing Hantzsch ester as a hydrogen source at room temperature was developed. This method featured a wide substrate scope and great functional group compatibility, providing facile and robust process to alkyl sulfonyl fluorides including enzyme inhibitors, natural products and drugs derivatives in up to 99% yield. Further derivatization of resultant

  在室温下，使用汉茨sch酯作为氢源，开发了一种可见光诱导的将1°，2°和3°烷基碘还原加入乙磺酰氟的方法。该方法具有广泛的底物范围和出色的官能团相容性，可为烷基磺酰氟（包括酶抑制剂，天然产物和药物衍生物）提供简便而稳固的工艺，产率高达99％。还可以通过氟化硫交换（SuFEx）反应实现对生成的脂肪族磺酰氟的进一步衍生，以传递磺酸盐和磺酰胺作为药物化学的优先基序。
• 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.