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, BARBARA; PELLOWSKA-JANUSZEK, LUCYNA; SAMASZKO-FIERTEK, JUSTYNA; SLUSARZ, RAFAL; WAKIEC, ROLAND; and MADAJ, JANUSZ (2019) "Efficient synthesis and antifungal investigation of nucleosides' quaternary ammonium salt derivatives," Turkish Journal of Chemistry: Vol. 43: No. 1, Article 14. https://doi.org/10.3906/kim-1808-34
Available at: https://journals.tubitak.gov.tr/chem/vol43/iss1/14