Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2 H -tetrazoles

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 57; no. 4; p. 442
• Main Authors: Mikolaichuk, Olga V, Zarubaev, Vladimir V, Muryleva, Anna А, Esaulkova, Yana L, Spasibenko, Daria V, Batyrenko, Alina А, Kornyakov, Ilya V, Trifonov, Rostislav Е
• Format: Journal Article
• Language: English
• Published: United States 2021
• Subjects: X-ray structural analysis; anti-influenza activity; nitration; 2-(adamantan-1-yl)-5-aryl-2H-tetrazoles; adamantylation
• ISSN: 0009-3122; 1573-8353

The reaction of 5-aryl- -tetrazoles with adamantan-1-ol in concentrated sulfuric acid proceeds regioselectively with the formation of the corresponding 2-adamantyl-5-aryl-2 -tetrazoles. Nitration of these compounds leads to 2-(adamantan-1-yl)-5-(3-nitroaryl)-2 tetrazoles. The structures and composition of the obtained novel 2-adamantyl-5-aryltetrazoles were proven by IR spectroscopy, H and 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. 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)-2 -tetrazol-5-yl]-6-bromo-4-nitroaniline is significantly higher (SI 11) than that of the reference drug rimantadine (SI 5). The online version contains supplementary material available at 10.1007/s10593-021-02931-5.