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Russian Chemical Bulletin

, Volume 67, Issue 4, pp 712–720 | Cite as

Synthesis and study of new phenolic antioxidants with nitroaromatic and heterocyclic substituents

  • O. V. Mikhalev
  • D. B. Shpakovsky
  • Yu. A. Gracheva
  • T. A. Antonenko
  • D. V. Albov
  • L. A. Aslanov
  • E. R. Milaeva
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Abstract

New polyfunctional aromatic, nitroaromatic, and heterocyclic compounds linked to the 2,6-di-tert-butylphenol moiety via –NH–, –C(O)NH–, –S–, or–C=N– spacers were synthesized. These structures provide intramolecular charge transfer (ICT) and exhibit antioxidant activity. The structures of the new compounds were established by X-ray diffraction. The novel compounds were evaluated for antioxidant activity using the DPPH assay. The presence of the 2,4,6-trinitrophenyl moiety in combination with the –NH– spacer leads to a considerable increase in the antioxidant activity of 2,6-di-tert-butylphenols. These compounds are also weak lipoxygenase inhibitors. The results of this study provide an opportunity to search for new types of antioxidants with ICT.

Key words

2,6-di-tert-butylphenol antioxidant activity DPPH assay intramolecular charge transfer X-ray diffraction analysis 

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • O. V. Mikhalev
    • 1
  • D. B. Shpakovsky
    • 1
  • Yu. A. Gracheva
    • 1
  • T. A. Antonenko
    • 1
  • D. V. Albov
    • 1
  • L. A. Aslanov
    • 1
  • E. R. Milaeva
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityMoscow, Russian FederationRussia

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