Synthesis and antiviral activity of novel 3-substituted pyrazolinium salts

For the first time, convenient methods for the preparation of pyrazoline N -alkylidene salts based on terpene (camphor, camphorquinone, carvone) ketones, cage (adamantanone and norcamphor) ketones, and natural aldehydes (carvone and myrtenal) allowing the isolation of stable pyrazolinium salts in in...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2021-04, Vol.57 (4), p.432-441
Main Authors: Vorozhtsov, Nikolai O., Yarovaya, Olga I., Roznyatovskii, Vitalii A., Tarasevich, Boris N., Kozlovskaya, Yuliya A., Petkova, Aneliya I., Slita, Aleksander V., Sinegubova, Ekaterina O., Zarubaev, Vladimir V., Salakhutdinov, Nariman F., Beloglazkina, Elena K.
Format: Article
Language:English
Subjects:
Aldehydes
Alkylidene
Antiviral agents
Camphor
Chemistry
Chemistry and Materials Science
Ketones
Optimization
Organic Chemistry
Pharmacy
Synthesis
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Summary:For the first time, convenient methods for the preparation of pyrazoline N -alkylidene salts based on terpene (camphor, camphorquinone, carvone) ketones, cage (adamantanone and norcamphor) ketones, and natural aldehydes (carvone and myrtenal) allowing the isolation of stable pyrazolinium salts in individual form were proposed. Optimization of the conditions for the synthesis of the target products was carried out. The antiviral activity of the synthesized salts was studied; among the tested compounds 1-bornylidene-3-phenylpyrazolinium tetrafluoroborate (IC 50 6.2 μM, SI 107) exhibited the greatest activity against influenza A/Puerto Rico/8/34 (H1N1) virus.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-021-02921-7