3-Hydroxyquinolin-2(1H)-ones As Inhibitors of Influenza A Endonuclease

被引：46
|
作者：
Sagong, Hye Yeon [1 ]
Parhi, Ajit [1 ]
Bauman, Joseph D. [2 ,3 ]
Patel, Disha [1 ]
Vijayan, R. S. K. [2 ,3 ]
Das, Kalyan [2 ,3 ]
Arnod, Eddy [2 ,3 ]
LaVoie, Edmond J. [1 ]
机构：
[1] Rutgers State Univ, Ernest Mario Sch Pharm, Dept Med Chem, Piscataway, NJ 08854 USA
[2] Rutgers State Univ, Ctr Adv Biotechnol & Med, Piscataway, NJ 08854 USA
[3] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
来源：
ACS MEDICINAL CHEMISTRY LETTERS | 2013年 / 4卷 / 06期
关键词：
antiviral; influenza A; quinolinones; 3-hydroxyquinolin-2-ones; endonuclease; CRYSTAL-STRUCTURE; VIRUS; PA;
D O I：
10.1021/ml4001112
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Several 3-hydroxyquinolin-2(1H)-ones. derivatives were synthesized and evaluated as inhibitors of 2009 pandemic H1N1 influenza A endonuclease. All five of the monobrominated 3-hydroxyquinolin (1H)-2-ones derivatives were synthesized. Suzuki-coupling of p-fluorophenylboronic acid with each of these brominated derivatives provided the respective p-fluorophenyl hydroxyquinolin (1H)-2-ones. In addition to 3-hydroxyquinolin-2 (1H)-one, its 4-methyl, 4-phenyl, 4-methyl-7-(p-fluorophenyl), and 4-phenyl-7-(p-fluorophenyl) derivatives were also synthesized. Comparative studies on their relative activity revealed that both 6- and 7-(p-fluorophenyl)-3- hydroxyquinolin-2(1H)-one are among the more potent inhibitors of H1N1 influenza A endonuclease. An X-ray crystal structure of 7-(p-fluorophenyl)-3-hydroxyquinolin-2(1H)-one complexed to the influenza endonuclease revealed that this molecule chelates to two metal ions at the active site of the enzyme.
引用
收藏
页码：547 / 550
页数：4
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