Synthesis and study of new phenolic antioxidants with nitroaromatic and heterocyclic substituents
- Authors: Mikhalev O.V.1, Shpakovsky D.B.1, Gracheva Y.A.1, Antonenko T.A.1, Albov D.V.1, Aslanov L.A.1, Milaeva E.R.1
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Affiliations:
- M. V. Lomonosov Moscow State University
- Issue: Vol 67, No 4 (2018)
- Pages: 712-720
- Section: Full Article
- URL: https://journals.rcsi.science/1066-5285/article/view/242445
- DOI: https://doi.org/10.1007/s11172-018-2127-2
- ID: 242445
Cite item
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.
About the authors
O. V. Mikhalev
M. V. Lomonosov Moscow State University
Author for correspondence.
Email: mov@med.chem.msu.ru
Russian Federation, 1, Build. 3, Leninskie Gory, Moscow, Russian Federation, 119991
D. B. Shpakovsky
M. V. Lomonosov Moscow State University
Email: mov@med.chem.msu.ru
Russian Federation, 1, Build. 3, Leninskie Gory, Moscow, Russian Federation, 119991
Yu. A. Gracheva
M. V. Lomonosov Moscow State University
Email: mov@med.chem.msu.ru
Russian Federation, 1, Build. 3, Leninskie Gory, Moscow, Russian Federation, 119991
T. A. Antonenko
M. V. Lomonosov Moscow State University
Email: mov@med.chem.msu.ru
Russian Federation, 1, Build. 3, Leninskie Gory, Moscow, Russian Federation, 119991
D. V. Albov
M. V. Lomonosov Moscow State University
Email: mov@med.chem.msu.ru
Russian Federation, 1, Build. 3, Leninskie Gory, Moscow, Russian Federation, 119991
L. A. Aslanov
M. V. Lomonosov Moscow State University
Email: mov@med.chem.msu.ru
Russian Federation, 1, Build. 3, Leninskie Gory, Moscow, Russian Federation, 119991
E. R. Milaeva
M. V. Lomonosov Moscow State University
Email: mov@med.chem.msu.ru
Russian Federation, 1, Build. 3, Leninskie Gory, Moscow, Russian Federation, 119991