8-Hydroxyquinoline-2-Carboxanilides as Antiviral Agents Against Avian Influenza Virus

Jiri Kos, Chuen Fai KU, Iva Kapustikova, Michal Oravec, Hongjie ZHANG*, Josef Jampilek

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

Series of thirty-two mono-, di- and tri-substituted 8-hydroxyquinoline-2-carboxanilides were prepared by microwave-assisted synthesis. The compounds were characterized, and their lipophilicity was experimentally determined. Primary in vitro screening of the cytotoxicity of all the synthesized compounds was performed using adenocarcinomic human alveolar basal epithelial cells (A549), and determined nontoxic compounds were then tested for their activity against highly pathogenic H5N1 avian influenza virus. 8-Hydroxy-N-(3,4,5-trichlorophenyl)quinoline-2-carboxamide, N-(3-chloro-2-fluorophenyl)-8-hydroxyquinoline-2-carboxamide and N-(3,4-dichlorophenyl)-8-hydroxyquinoline-2-carboxamide demonstrated the highest activity within the investigated series (IC 50  = 11.3, 21.2 and 31.2 μM, respectively), while N-(4-chloro-2-fluorophenyl)-8-hydroxyquinoline-2-carboxamide expressed the highest cytotoxic effect (CC 50  = 31.6 μM). In general, the inhibitory activity of the compounds depends on the position of halogen substituents on the anilide ring and is also affected by the lipophilicity and electron properties of individual substituents of the anilide part of the molecule. The structure-activity relationships are discussed.

Original languageEnglish
Pages (from-to)4582-4587
Number of pages6
JournalChemistrySelect
Volume4
Issue number15
DOIs
Publication statusPublished - 24 Apr 2019

Scopus Subject Areas

  • Chemistry(all)

User-Defined Keywords

  • cytotoxicity
  • H5N1 influenza virus
  • hydroxyquinolinecarboxanilides
  • lipophilicity
  • microwave-assisted synthesis
  • structure-activity relationships

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