Synthesis and Antiviral Activity of N-Heterocyclic Hydrazine Derivatives of Camphor and Fenchone

Synthesis and Antiviral Activity of N-Heterocyclic Hydrazine Derivatives of Camphor and Fenchone Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 2021, Volume: 57, Pages: 455–461 Pages count : DOI: 10.1007/s10593-021-02923-5

Tags

antiviral activity; camphor; fenchone; heterocycles; hydrazones

Authors

Kovaleva K.S. ¹ , Yarovaya O.I. ¹ , Gatilov Yu.V. ¹ , Slita A.V. ² , Esaulkova Y.L. ² , Zarubaev V.V. ² , Rudometova N.B. ³ , Shcherbakova N.S. ³ , Shcherbakov D.N. ³ , Salakhutdinov N.F. ¹

Affiliations

1	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave, Novosibirsk, 630090, Russian Federation
2	Saint Petersburg Pasteur Research Institute of Epidemiology and Microbiology, 14 Mira St, Saint Petersburg, 197101, Russian Federation
3	State Research Center of Virology and Biotechnology “Vector”, Federal Service for Surveillance on Consumer Rights Protection and Human Wellbeing, Koltsovo, Novosibirsk Oblast 630559, Russian Federation

[Figure not available: see fulltext.] Alkylation of the primary amino group of hydrazones of (+)-camphor and (–)-fenchone with dihaloalkanes leading to the production of novel nitrogen-containing heterocyclic derivatives was investigated. It was shown that the reaction of hydrazones with 1,2-ethanedithiol in the presence of formaldehyde with the addition of 5% Sm(NO3)3·6H2O leads to the formation of compounds containing the 1,5,3-dithiazepane fragment. The method developed by us offers the advantage of the use of commercially available reagents and good yields in the synthesis of hydrazone heterocyclic derivatives. Studies of antiviral activity have shown that camphor-based N-heterocyclic compounds can be considered promising agents with activity against influenza A. © 2021, Springer Science+Business Media, LLC, part of Springer Nature.

Kovaleva K.S. , Yarovaya O.I. , Gatilov Y.V. , Slita A.V. , Esaulkova Y.L. , Zarubaev V.V. , Rudometova N.B. , Shcherbakova N.S. , Shcherbakov D.N. , Salakhutdinov N.F.
Synthesis and Antiviral Activity of N-Heterocyclic Hydrazine Derivatives of Camphor and Fenchone
Chemistry of Heterocyclic Compounds. 2021. V.57. P.455–461. DOI: 10.1007/s10593-021-02923-5 WOS Scopus РИНЦ

Published print:	Apr 1, 2021
Published online:	May 12, 2021

Web of science	WOS:000649250900001
Scopus	2-s2.0-85105850038
Elibrary	46090627
OpenAlex	W3162839137