Author: Mikolaichuk, Olga V.; Zarubaev, Vladimir V.; Muryleva, Anna Ð.; Esaulkova, Yana L.; Spasibenko, Daria V.; Batyrenko, Alina Ð.; Kornyakov, Ilya V.; Trifonov, Rostislav Е.
Title: Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles Cord-id: d9ccxw9q Document date: 2021_5_26
ID: d9ccxw9q
Snippet: [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 structur
Document: [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.
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