SYNTHESIS AND ANTIVIRAL ACTIVITY OF N-HETEROCYCLIC HYDRAZINE DERIVATIVES OF CAMPHOR AND FENCHONE

Authors

  • Ксения С. Ковалева N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
  • Ольга И. Яровая N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
  • Юрий В. Гатилов N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
  • Александр В. Слита Saint Petersburg Pasteur Research Institute of Epidemiology and Microbiology, 14 Mira St., Saint Petersburg 197101, Russia
  • Яна Л. Есаулкова Saint Petersburg Pasteur Research Institute of Epidemiology and Microbiology, 14 Mira St., Saint Petersburg 197101, Russia
  • Владимир В. Зарубаев Saint Petersburg Pasteur Research Institute of Epidemiology and Microbiology, 14 Mira St., Saint Petersburg 197101, Russia
  • Надежда Б. Рудометова State Research Center of Virology and Biotechnology ''Vector'', Federal Service for Surveillance on Consumer Rights Protection and Human Wellbeing, Koltsovo 630559, Novosibirsk Oblast, Russia
  • Надежда С. Щербакова State Research Center of Virology and Biotechnology ''Vector'', Federal Service for Surveillance on Consumer Rights Protection and Human Wellbeing, Koltsovo 630559, Novosibirsk Oblast, Russia
  • Дмитрий Н. Щербаков State Research Center of Virology and Biotechnology ''Vector'', Federal Service for Surveillance on Consumer Rights Protection and Human Wellbeing, Koltsovo 630559, Novosibirsk Oblast, Russia
  • Нариман Ф. Салахутдинов N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia

DOI:

https://doi.org/10.1007/6063

Keywords:

camphor, fenchone, heterocycles, hydrazones, antiviral activity.

Abstract

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.

Published

2021-05-05