A series of tris(5‐aryl‐1H‐tetrazol‐1‐yl)methanes (3a‐3g) and 2‐dichloromethyl‐5‐aryl‐2H‐tetrazoles (4a‐4d) were synthesized by reaction of 5‐aryl‐NH‐tetrazoles with trichloromethane in strong aqueous basic condition. The compounds obtained were fully characterized by means of HRESI‐MS, 1H and 13C{1H} NMR spectroscopies, as well as by single‐crystal X‐ray diffraction (for 3a, 3b, 4d). Inspection of the X‐ray diffraction data and Hirshfeld surface analysis for tris(5‐aryl‐1H‐tetrazol‐1‐yl)methanes 3a,b and 2‐dichloromethyl‐5‐aryl‐2H‐tetrazole 4d showed the presence of noncovalent π‐hole•••lone pair and π‐hole•••π interactions involving electrophilic tetrazole carbon atom.
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).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.