Efficient synthesis and antifungal investigation of nucleosides' quaternary ammonium salt derivatives

Authors: BARBARA DMOCHOWSKA, LUCYNA PELLOWSKA-JANUSZEK, JUSTYNA SAMASZKO-FIERTEK, RAFAL SLUSARZ, ROLAND WAKIEC, JANUSZ MADAJ

Abstract: Quaternary ammonium salts are a group of compounds with diverse biological properties, the most important of which are their antiviral, antibacterial, and antifungal activities. The quaternization reactions of 5'-$O$-tosyl derivatives of uridine and thymidine with triethylamine, trimethylamine, 4-($N$,$N$-dimethylamino)pyridine, 2-methylpyridine, and pyridine are described in this article. Two of the synthesized compounds are exceptional because they are first of this type that demonstrate concentration-dependent antifungal in vitro activity against two species of the genus Candida in minimal YNB-SG medium. The experimental results have been extended by adding full atom molecular dynamics simulations and substrates and products energies evaluation.

Keywords: Quaternary ammonium salts, uridine-5\textquotesingle-ammonium derivatives, thymidine-5\textquotesingle-ammonium derivatives

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