1128052-15-2

Upstream product

• 142348-93-4 5,12-(dimethyl)thioquinanthrenediinium bis(chloride) 
• 98-88-4 benzoyl chloride 
• 142349-08-4 1-methyl-3-(mercapto)quinoline-4(1H)-thione 

Downstream Products

• 1128052-22-1 3-benzoylsulfanyl-1-methyl-4-methylsulfanyl-quinolinium methyl sulfate 

Relevant academic research and scientific papers

Synthesis and antimicrobial activity of sulfur derivatives of quinolinium salts

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).

3-Acylsulfanyl-1-methyl-4-methylsulfanyl-quinolinium salts and their transformation into 4-aminoquinolinium-3-thiolates and azaphenothiazine derivatives

3-Acylsulfanyl-1-methyl-4-methylsulfanyl-quinolinium methyl sulfates 3 were obtained via acylation of 1-methyl-3-sulfanyl-1H-quinoline-4-thione (1) in the presence of a base and subsequent alkylation with dimethyl sulfate. Reactions of 3-acylsulfanyl-1-methyl-4-methylsulfanyl-quinolinium chlorides 4 with primary aliphatic and aromatic amines led to 4-amino-1-methylquinolinium-3-thiolates (5). When the reactions of chlorides 4 with aniline were carried out in the presence of atmospheric oxygen, the 3-thiolate 5 formed in the first step of the reaction underwent cyclization to 5-methyl-12H-quino-[3,4-b][1,4] benzothiazinium chloride (6).