2-(3'-acetylbiphenyl-4-yl)acetonitrile | 1443159-76-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3'-acetylbiphenyl-4-yl)acetonitrile
• CAS: 1443159-76-9
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: KMUVXLAMKYKWCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(3'-acetylbiphenyl-4-yl)acetonitrile 在 三正丁基叠氮化锡 作用下， 以 1,4-二氧六环 为溶剂， 以76%的产率得到1-(4'-((1H(2H)-tetrazol-5-yl)methyl)biphenyl-3-yl)ethanone
  参考文献：
  名称：

  Biaryl tetrazolyl ureas as inhibitors of endocannabinoid metabolism: Modulation at the N-portion and distal phenyl ring

  摘要：

  In the present study, we have further extended the structure activity relationships for the tetrazolyl ureas class of compounds as potential FAAH and/or MAGL inhibitors, by replacing the dimethylamino group of the parent compounds 1 and 2 with bulkier groups or by introducing on the distal phenyl ring of 1 and 2 a selected set of substituents. Some of the new compounds (16, 20, 21, 25, and 28) inhibited FAAH potently (IC50 = 3.0-9.7 nM) and selectively (39- to more than 141-fold) over MAGL, while tetrazole 27 turned out to be a promising dual FAAH MAGL inhibitor of potential therapeutic use. Covalent docking studies on FAAH indicated that the binding modes of tetrazoles 1-32 did not display a unique pattern. The ability of tetrazoles 1-32 to act as TRPV1 and TRPA1 modulators was also investigated. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.005
• 作为产物：
  描述：

  4-碘苯基乙腈, 、 3-乙酰基苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 、 potassium bromide 作用下， 以 1,4-二氧六环 为溶剂， 以69%的产率得到2-(3'-acetylbiphenyl-4-yl)acetonitrile
  参考文献：
  名称：

  Biaryl tetrazolyl ureas as inhibitors of endocannabinoid metabolism: Modulation at the N-portion and distal phenyl ring

  摘要：

  In the present study, we have further extended the structure activity relationships for the tetrazolyl ureas class of compounds as potential FAAH and/or MAGL inhibitors, by replacing the dimethylamino group of the parent compounds 1 and 2 with bulkier groups or by introducing on the distal phenyl ring of 1 and 2 a selected set of substituents. Some of the new compounds (16, 20, 21, 25, and 28) inhibited FAAH potently (IC50 = 3.0-9.7 nM) and selectively (39- to more than 141-fold) over MAGL, while tetrazole 27 turned out to be a promising dual FAAH MAGL inhibitor of potential therapeutic use. Covalent docking studies on FAAH indicated that the binding modes of tetrazoles 1-32 did not display a unique pattern. The ability of tetrazoles 1-32 to act as TRPV1 and TRPA1 modulators was also investigated. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.005