Design, synthesis and anti-influenza virus activity of furan-substituted spirothiazolidinones

• Published in: Bioorganic chemistry Vol. 112; p. 104958
• Main Authors: Apaydın, Çağla Begüm, Tansuyu, Merve, Cesur, Zafer, Naesens, Lieve, Göktaş, Füsun
• Format: Journal Article
• Language: English
• Published: SAN DIEGO Elsevier Inc 01.07.2021; Elsevier
• Subjects: Antiviral activity; Biochemistry & Molecular Biology; Chemistry; Chemistry, Organic; Furan; İnfluenza virus; Life Sciences & Biomedicine; Physical Sciences; Science & Technology; Spirothiazolidinone; Synthesis; Spirothiazolidinone; Furan; İnfluenza virus; Synthesis; Antiviral activity; INFLUENZA; Influenza virus
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2021.104958

[Display omitted] •New N-(3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl)carboxamide derivatives were synthesized.•Compounds 3c and 3d had superior activity against influenza A/H3N2 virus.•Spirothiazolidinone moiety is important for antiviral activity. A new series of N-(3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl)carboxamides have been designed, synthesized and evaluated as antiviral agents. The compounds were prepared by condensation of 2-methylfuran-3-carbohydrazide, appropriate carbonyl compounds and sulfanyl acids. The new molecules were characterized by IR, 1H NMR, 13C NMR, mass spectrometry and elemental analysis. Six analogues proved to be active against influenza A/H3N2 virus, the two most protent analogues, 3c and 3d, having an EC50 value of about 1 µM. These findings help to define the SAR of spirothiazolidinone-based inhibitors of the influenza virus membrane fusion process.