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Publication Abstract from PubMed

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 3-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.

3-Hydroxyquinolin-2(1H)-ones As Inhibitors of Influenza A Endonuclease.,Sagong HY, Parhi A, Bauman JD, Patel D, Vijayan RS, Das K, Arnold E, LaVoie EJ ACS Med Chem Lett. 2013 May 7;4(6):547-50. doi: 10.1021/ml4001112. eCollection, 2013 Jun 13. PMID:24936242^[1]

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.