Laccase-Catalyzed 1,4-Dioxane-Mediated Synthesis of Belladine N-Oxides with Anti-Influenza A Virus Activity

Int J Mol Sci. 2021 Jan 29;22(3):1337. doi: 10.3390/ijms22031337.

Abstract

Belladine N-oxides active against influenza A virus have been synthetized by a novel laccase-catalyzed 1,4-dioxane-mediated oxidation of aromatic and side-chain modified belladine derivatives. Electron paramagnetic resonance (EPR) analysis confirmed the role of 1,4-dioxane as a co-oxidant. The reaction was chemo-selective, showing a high functional-group compatibility. The novel belladine N-oxides were active against influenza A virus, involving the early stage of the virus replication life cycle.

Keywords: 1,4-dioxane; EPR; N-oxides; Oxizymes; belladine derivatives; influenza A virus; laccase.

MeSH terms

  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Catalysis
  • Dioxanes / chemistry*
  • Humans
  • Influenza A virus / drug effects*
  • Influenza, Human / drug therapy
  • Influenza, Human / virology
  • Laccase / chemistry*
  • Oxidation-Reduction
  • Oxides / chemistry
  • Oxides / pharmacology*
  • Polyporaceae / enzymology*

Substances

  • Antiviral Agents
  • Dioxanes
  • Oxides
  • Laccase
  • 1,4-dioxane

Supplementary concepts

  • Trametes versicolor