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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Published inRussian journal of general chemistry Vol. 94; no. 8; pp. 1912 - 1929
Main Authors 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.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.08.2024
Springer Nature B.V
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
pyridoxine
and
quantum chemical calculations
antimycotic activity
selenium dioxide
antioxidant activity
pyridinone methides
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Summary: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.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363224080036