A novel and efficient synthesis of tocopheryl quinones by homogeneous and heterogeneous methyltrioxorhenium/hydrogen peroxide catalytic systems

Raffaele Saladino, Veronica Neri, Angela Farina, Claudia Crestini, Lucia Nencioni, Anna Teresa Palamara

Research output: Contribution to journalArticlepeer-review

Abstract

A convenient and efficient application of heterogeneous poly(4-vinylpyridine), poly(4-vinyl-pyridine N-oxide), and polystyrene/ methylrhenium trioxide systems for the selective oxidation of tocopherols and tocopherol derivatives to the corresponding ortho- and para-tocopherylquinones is described. Environment friendly, easily available, and low-cost hydrogen peroxide (H2O2) was used as the oxygen atom donor. The antiviral activity of the newly synthesized tocopherylquinones and their parent tocopherols against influenza A virus is also reported. On the basis of the biological assay, the activity of tocopherols against influenza virus is higher than that showed by the corresponding tocopherylquinones, thus suggesting, for the first time, a drawback effect of the oxidative metabolism on the antiviral activity of these compounds.

Original languageEnglish
Pages (from-to)321-331
Number of pages11
JournalAdvanced Synthesis and Catalysis
Volume350
Issue number2
DOIs
Publication statusPublished - Jan 2008

Keywords

  • Antiviral agents
  • Heterogeneous catalysis
  • Homogeneous catalysis
  • Hydrogen peroxide
  • Quinones
  • Rhenium

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Organic Chemistry
  • Catalysis

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