Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles
| Autor: | Ilya V. Kornyakov, Daria V. Spasibenko, Anna А Muryleva, Alina А Batyrenko, Rostislav Е Trifonov, Olga V. Mikolaichuk, Vladimir V. Zarubaev, Yana L Esaulkova |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Rimantadine
010405 organic chemistry Chemistry Aryl Organic Chemistry 2-(adamantan-1-yl)-5-aryl-2H-tetrazoles Infrared spectroscopy Sulfuric acid 010402 general chemistry Mass spectrometry nitration 01 natural sciences Medicinal chemistry anti-influenza activity Article 0104 chemical sciences chemistry.chemical_compound Nitration medicine adamantylation Thermal analysis Selectivity X-ray structural analysis medicine.drug |
| Zdroj: | Chemistry of Heterocyclic Compounds |
| ISSN: | 1573-8353 0009-3122 |
| Popis: | 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, 1H and 13C 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. |
| Databáze: | OpenAIRE |
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