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

Bioorg Chem. 2021 Jul:112:104958. doi: 10.1016/j.bioorg.2021.104958. Epub 2021 Apr 30.

Abstract

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.

Keywords: Antiviral activity; Furan; Spirothiazolidinone; Synthesis; İnfluenza virus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Furans / chemistry
  • Furans / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Docking Simulation
  • Molecular Structure
  • Orthomyxoviridae / drug effects*
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry
  • Spiro Compounds / pharmacology*
  • Structure-Activity Relationship
  • Thiazolidinediones / chemical synthesis
  • Thiazolidinediones / chemistry
  • Thiazolidinediones / pharmacology*

Substances

  • Antiviral Agents
  • Furans
  • Spiro Compounds
  • Thiazolidinediones