SYNTHESIS OF NAPHTHYL- AND ALKALOID-CONTAINING THIOUREAS
Abstract
Previously, we investigated the reactions of various isothiocyanates with cytisine, anabasine and ephedrine alkaloids [1]. In continuation of our research on the study of thiourea derivatives of alkaloids, we synthesized N-naphthylthiocarbamide derivatives based on the alkaloids piperidine (2), anabasine (3), cytisine (4), l-ephedrine (5), d-pseudoephedrine (6) and salsolin (7), which were obtained by the interaction of alkaloids with naphthylisothiocyanate (1) in an ethanol (Figure 1). The composition and structure of the synthesized naphthyl-containing thioureas are confirmed by data from elemental analysis, IR, NMR 1H, 13C spectroscopy, and X-ray structural analysis. Various studies of the bioactivity of the obtained compounds have been conducted, including an assessment of their hemorheological and antiviral properties. As a result of screening, it was found that compound (3) exhibits a pronounced ability to reduce blood viscosity and high virus-inhibiting activity (the reference standard is remantadine and tamiflu), which indicates the prospects for further study of it as a potential active agent.
References
- O. A. Nurkenov, Zh. B. Satpaeva, S. D. Fazylov, T. M. Seilkhanov, K. M. Turdybekov, D. M. Turdybekov, S. B. Akhmetova, A. S. Makhmutova, A. M. Gazaliev. (2016). Synthesis of Thiourea Derivatives of the Alkaloids Anabasine, Cytisine, and d-Pseudoephedrine. Crystal Structure of N-ethyl-N-Anabasinocarbothioamide.Chemistry of Natural Compounds.[Crossref]
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