Molecules (Jan 2018)

Synthesis and Antimicrobial Activity of Sulfur Derivatives of Quinolinium Salts

  • Anna Empel,
  • Ewa Kisiel,
  • Robert D. Wojtyczka,
  • Małgorzata Kępa,
  • Danuta Idzik,
  • Aleksander Sochanik,
  • Tomasz J. Wąsik,
  • Andrzej Zięba

DOI
https://doi.org/10.3390/molecules23010218
Journal volume & issue
Vol. 23, no. 1
p. 218

Abstract

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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).

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