Synthesis and Biological Activity of 2,6-Substituted Pyridoxine Derivatives. Unusual Catalytic Role of Selenium Dioxide in the Formation of Pyridinone Methides

Among the seven-membered ketals of pyridoxine containing hydroxymethyl groups in various positions of the pyridine ring, an unusual ability of selenium dioxide to catalyze the reaction of nucleophilic substitution of the hydroxyl group by N , O -nucleophiles was found. Quantum chemical calculations...

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Veröffentlicht in:Russian journal of general chemistry 2024-08, Vol.94 (8), p.1912-1929
Hauptverfasser: Khaziev, R. M., Platonova, E. A., Bondar, O. V., Khristolyubova, A. S., Serov, N. Y., Lisovskaya, S. A., Vafina, R. M., Shtyrlin, V. G., Shtyrlin, N. V., Islamov, D. R., Burilov, V. A., Romanova, E. I., Shtyrlin, Yu. G.
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container_end_page 1929
container_issue 8
container_start_page 1912
container_title Russian journal of general chemistry
container_volume 94
creator Khaziev, R. M.
Platonova, E. A.
Bondar, O. V.
Khristolyubova, A. S.
Serov, N. Y.
Lisovskaya, S. A.
Vafina, R. M.
Shtyrlin, V. G.
Shtyrlin, N. V.
Islamov, D. R.
Burilov, V. A.
Romanova, E. I.
Shtyrlin, Yu. G.
description Among the seven-membered ketals of pyridoxine containing hydroxymethyl groups in various positions of the pyridine ring, an unusual ability of selenium dioxide to catalyze the reaction of nucleophilic substitution of the hydroxyl group by N , O -nucleophiles was found. Quantum chemical calculations have shown the possibility of the formation of selenium dioxide adducts with substrates and the formation of reactive intermediates— ortho- and para- pyridinone methides. The antioxidant and antimycotic activity of the obtained compounds was determined.
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ispartof Russian journal of general chemistry, 2024-08, Vol.94 (8), p.1912-1929
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subjects Adducts
Biological activity
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Dioxides
Hydroxyl groups
Nucleophiles
Pyridoxine
Quantum chemistry
Selenium dioxide
Substitution reactions
Substrates
title Synthesis and Biological Activity of 2,6-Substituted Pyridoxine Derivatives. Unusual Catalytic Role of Selenium Dioxide in the Formation of Pyridinone Methides
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