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

Barbara Dmochowska , Lucyna Pellowska-Januszek , Justyna Samaszko-Fiertek , Rafał Ślusarz , Roland Wakieć , Janusz Madaj

Abstract

Quaternary ammonium salts are a group of compounds with diverse biological properties, the most importantof which are their antiviral, antibacterial, and antifungal activities. The quaternization reactions of 5'-O-tosyl derivativesof uridine and thymidine with triethylamine, trimethylamine, 4-(N,N-dimethylamino)pyridine, 2-methylpyridine, andpyridine are described in this article. Two of the synthesized compounds are exceptional because they are first of thistype that demonstrate concentration-dependent antifungal in vitro activity against two species of the genusCandidain minimal YNB-SG medium. The experimental results have been extended by adding full atom molecular dynamicssimulations and substrates and products energies evaluation.
Author Barbara Dmochowska (FCh / DOCh / LCCh)
Barbara Dmochowska,,
- Laboratory of Carbohydrate Chemistry
, Lucyna Pellowska-Januszek (FCh / DOCh / LCCh)
Lucyna Pellowska-Januszek,,
- Laboratory of Carbohydrate Chemistry
, Justyna Samaszko-Fiertek (FCh / DOCh / LCCh)
Justyna Samaszko-Fiertek,,
- Laboratory of Carbohydrate Chemistry
, Rafał Ślusarz (FCh / DOCh / LCCh)
Rafał Ślusarz,,
- Laboratory of Carbohydrate Chemistry
, Roland Wakieć
Roland Wakieć,,
-
, Janusz Madaj (FCh / DOCh / LCCh)
Janusz Madaj,,
- Laboratory of Carbohydrate Chemistry
Journal seriesTurkish Journal of Chemistry, ISSN 1300-0527, (A 20 pkt)
Issue year2019
Vol43
Pages157-171
Publication size in sheets0.7
Keywords in EnglishQuaternary ammonium salts, uridine-5'-ammonium derivatives, thymidine-5'-ammonium derivatives
ASJC Classification1600 General Chemistry
DOIDOI:10.3906/kim-1808-34
URL http://journals.tubitak.gov.tr/chem/issues/kim-19-43-1/kim-43-1-14-1808-34.pdf
Languageen angielski
LicenseJournal (articles only); published final; Uznanie Autorstwa (CC-BY); with publication
Score (nominal)20
ScoreMinisterial score = 20.0, 24-07-2019, ArticleFromJournal
Publication indicators WoS Citations = 0; Scopus SNIP (Source Normalised Impact per Paper): 2016 = 0.616; WoS Impact Factor: 2017 = 1.377 (2) - 2017=1.342 (5)
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