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.

DOI

10.3906/kim-1808-34

Keywords

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

First Page

157

Last Page

171

Recommended Citation

DMOCHOWSKA, B, PELLOWSKA-JANUSZEK, L, SAMASZKO-FIERTEK, J, SLUSARZ, R, WAKIEC, R, & MADAJ, J (2019). Efficient synthesis and antifungal investigation of nucleosides' quaternary ammonium salt derivatives. Turkish Journal of Chemistry 43 (1): 157-171. https://doi.org/10.3906/kim-1808-34