title: Synthesis and in vitro antimicrobial activity of 1-methyl-3-sulfonylthio-4-aminoquinolinium chlorides.
abstract: Synthesis and in vitro antimicrobial activity (MIC) of novel 1-methyl-3-sulfonylthio-4-aminoquinolinium chlorides 2 are described. Compounds 2 were obtained in the reaction of 1-methyl-4-aminoquinolinium 3-thiolates 1 with sulfonyl chlorides. Antimicrobial activity of compounds 2 was investigated using Gram-positive Staphylococcus aureus, Staphylococcus saprophyticus, Staphylococcus epidermidis, Micrococcus luteus, Enterococcus faecalis, Bacillus subtilis, Corynebacterium pseudodiphtericum and Gram-negative Escherichia coil, Klebsiella pneumoniae, Proteus vulgaris, Serratia marcescens, Citrobacter freundii, Pseudomonas aeruginosa strains as well as Candida albicans. The investigated compounds exhibited growth-inhibitory activity towards Gram-positive bacteria in the 4-64 microg/mL range whereas that towards Gram-negative bacteria covered the 128-1024 microg/mL range. The highest activity was shown by compound 2c, featuring a phenylsulfonylthio substituent in the 3-quinoline position and a 4-chlorophenylamine group in the position 4. All of the investigated compounds 2 showed antifungal activity in the 32-128 microg/mL range. Correlations between antimicrobial activity and chemical structure of the tested compounds were observed.
authors.affiliation: Department of Organic Chemistry, The Medical University of Silesia, Jagiellońska 4, 41-200 Sosnowiec, Poland. zieba@sum.edu.pl
authors.forename: Andrzej
authors.initials: A
authors.lastname: Zieba
authors.forename: Robert D
authors.initials: RD
authors.lastname: Wojtyczka
authors.forename: Danuta
authors.initials: D
authors.lastname: Idzik
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Kepa
mesh_terms: D000634:Aminoquinolines / Q000138:chemical synthesis* / Q000494:pharmacology*; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects / Q000254:growth & development; D004305:Dose-Response Relationship, Drug; D006090:Gram-Negative Bacteria / Q000187:drug effects / Q000254:growth & development; D006094:Gram-Positive Bacteria / Q000187:drug effects / Q000254:growth & development; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011806:Quinolinium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000634:Aminoquinolines; D000890:Anti-Infective Agents; D011806:Quinolinium Compounds; C001920:4-aminoquinoline