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Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles
[Image: see text] The reaction of 5-aryl-NH-tetrazoles with adamantan-1-ol in concentrated sulfuric acid proceeds regioselectively with the formation of the corresponding 2-adamantyl-5-aryl-2H-tetrazoles. Nitration of these compounds leads to 2-(adamantan-1-yl)-5-(3-nitroaryl)-2Htetrazoles. The stru...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer US
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8149581/ https://www.ncbi.nlm.nih.gov/pubmed/34054132 http://dx.doi.org/10.1007/s10593-021-02931-5 |
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author | Mikolaichuk, Olga V. Zarubaev, Vladimir V. Muryleva, Anna А. Esaulkova, Yana L. Spasibenko, Daria V. Batyrenko, Alina А. Kornyakov, Ilya V. Trifonov, Rostislav Е. |
author_facet | Mikolaichuk, Olga V. Zarubaev, Vladimir V. Muryleva, Anna А. Esaulkova, Yana L. Spasibenko, Daria V. Batyrenko, Alina А. Kornyakov, Ilya V. Trifonov, Rostislav Е. |
author_sort | Mikolaichuk, Olga V. |
collection | PubMed |
description | [Image: see text] The reaction of 5-aryl-NH-tetrazoles with adamantan-1-ol in concentrated sulfuric acid proceeds regioselectively with the formation of the corresponding 2-adamantyl-5-aryl-2H-tetrazoles. Nitration of these compounds leads to 2-(adamantan-1-yl)-5-(3-nitroaryl)-2Htetrazoles. The structures and composition of the obtained novel 2-adamantyl-5-aryltetrazoles were proven by IR spectroscopy, (1)H and (13)C NMR spectroscopy, high-resolution mass spectrometry, and also by X-ray structural analysis. According to the simultaneous thermal analysis data, the obtained compounds are thermally stable up to a temperature of about 150°C. In vitro studies have shown that some of the 2-adamantyl-5-aryltetrazoles exhibit moderate inhibitory activity against influenza A (H1N1) virus. The antiviral selectivity index (SI) of 2-[2-(adamantan-1-yl)-2H-tetrazol-5-yl]-6-bromo-4-nitroaniline is significantly higher (SI 11) than that of the reference drug rimantadine (SI 5). SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s10593-021-02931-5. |
format | Online Article Text |
id | pubmed-8149581 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Springer US |
record_format | MEDLINE/PubMed |
spelling | pubmed-81495812021-05-26 Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles Mikolaichuk, Olga V. Zarubaev, Vladimir V. Muryleva, Anna А. Esaulkova, Yana L. Spasibenko, Daria V. Batyrenko, Alina А. Kornyakov, Ilya V. Trifonov, Rostislav Е. Chem Heterocycl Compd (N Y) Article [Image: see text] The reaction of 5-aryl-NH-tetrazoles with adamantan-1-ol in concentrated sulfuric acid proceeds regioselectively with the formation of the corresponding 2-adamantyl-5-aryl-2H-tetrazoles. Nitration of these compounds leads to 2-(adamantan-1-yl)-5-(3-nitroaryl)-2Htetrazoles. The structures and composition of the obtained novel 2-adamantyl-5-aryltetrazoles were proven by IR spectroscopy, (1)H and (13)C NMR spectroscopy, high-resolution mass spectrometry, and also by X-ray structural analysis. According to the simultaneous thermal analysis data, the obtained compounds are thermally stable up to a temperature of about 150°C. In vitro studies have shown that some of the 2-adamantyl-5-aryltetrazoles exhibit moderate inhibitory activity against influenza A (H1N1) virus. The antiviral selectivity index (SI) of 2-[2-(adamantan-1-yl)-2H-tetrazol-5-yl]-6-bromo-4-nitroaniline is significantly higher (SI 11) than that of the reference drug rimantadine (SI 5). SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s10593-021-02931-5. Springer US 2021-05-26 2021 /pmc/articles/PMC8149581/ /pubmed/34054132 http://dx.doi.org/10.1007/s10593-021-02931-5 Text en © Springer Science+Business Media, LLC, part of Springer Nature 2021 This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic. |
spellingShingle | Article Mikolaichuk, Olga V. Zarubaev, Vladimir V. Muryleva, Anna А. Esaulkova, Yana L. Spasibenko, Daria V. Batyrenko, Alina А. Kornyakov, Ilya V. Trifonov, Rostislav Е. Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles |
title | Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles |
title_full | Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles |
title_fullStr | Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles |
title_full_unstemmed | Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles |
title_short | Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles |
title_sort | synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2h-tetrazoles |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8149581/ https://www.ncbi.nlm.nih.gov/pubmed/34054132 http://dx.doi.org/10.1007/s10593-021-02931-5 |
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