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Molecules 2018, 23(1), 218; https://doi.org/10.3390/molecules23010218

Synthesis and Antimicrobial Activity of Sulfur Derivatives of Quinolinium Salts

1
Department of Organic Chemistry, School of Pharmacy and Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, Jagiellońska 4, 41-200 Sosnowiec, Poland
2
Department and Institute of Microbiology and Virology, School of Pharmacy and Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, Jagiellońska 4, 41-200 Sosnowiec, Poland
3
Center for Translational Research and Molecular Biology of Cancer, Maria Skłodowska-Curie Mamorial Cancer Center and Institute of Oncology, Wybrzeże AK 15, 44-101 Gliwice, Poland
*
Author to whom correspondence should be addressed.
Received: 7 December 2017 / Revised: 13 January 2018 / Accepted: 18 January 2018 / Published: 20 January 2018
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A novel method for cleavage of the dithiine ring in 5,12-(dimethyl)-thioqinantrenium bis-chloride 1 “via” reaction with sodium hydrosulfide leads to 1-methyl-3-mercaptoquinoline-4(1H)-thione 2. Further transformation of thiol and thione functions of compound 2 leads to a series of sulfide and disulfide derivatives of quinolinium salts 4 and 6. 1-Methyl-4-chloro-3-benzylthioquinoline chloride 8 was obtained by N-alkylating 4-chloro-3-benzylthioquinoline using dimethyl sulfate. Antimicrobial activity of the obtained compounds was investigated using six Gram-positive and six Gram-negative bacterial strains, as well as Candida albicans yeast. Greater activity was demonstrated towards Gram-positive strains. MIC values for compounds and with benzylthio 4d and benzoylthio 4f substituents in 3-quinoline position were found to be in the 0.5–1 μg/mL range, at a level similar to that of ciprofloxacin (reference). Compounds 4d and 4f also demonstrated interesting antifungal properties (MIC = 1). View Full-Text
Keywords: quinolinium salts; antimicrobial activity; minimal inhibitory concentration quinolinium salts; antimicrobial activity; minimal inhibitory concentration
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
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Empel, A.; Kisiel, E.; Wojtyczka, R.D.; Kępa, M.; Idzik, D.; Sochanik, A.; Wąsik, T.J.; Zięba, A. Synthesis and Antimicrobial Activity of Sulfur Derivatives of Quinolinium Salts. Molecules 2018, 23, 218.

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