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SYNTHESIS, STRUCTURE, AND ANTIVIRAL PROPERTIES OF NOVEL 2-ADAMANTYL-5-ARYL-2H-TETRAZOLES

Ольга В. Миколайчук, Владимир В. Зарубаев, Анна А. Мурылева, Яна Л. Есаулкова, Дарья В. Спасибенко, Алина А. Батыренко, Илья В. Корняков, Ростислав Е. Трифонов
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Abstract


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)-2H-tetrazoles. 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).

Keywords


2-(adamantan-1-yl)-5-aryl-2H-tetrazoles; adamantylation; anti-influenza activity; nitration; X-ray structural analysis.

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