Abstract
The aim of this study was to evaluate the influence of pharmacophores having naphthylamine and nitro groups on the antimicrobial (antibacterial and antifungal) activity of thiazolidinone derivatives. The initial 5-substituted-2-methylmercaptothiazolidin-4-ones were subjected to S-demethylation to yield 2-amino-substituted thiazolidinones. 4-Nitro-1-naphthylamine, nitrofuran aldehydes, and nitrobenzene aldehydes were used as pharmacophoric compounds having amino or aldehyde groups. Antimicrobial (antibacterial and antifungal) activity of the new compounds was tested in vitro against bacterial cultures - Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Klebsiella pneumoniae - and fungal cultures - Candida albicans, Candida glabrata, Candida krusei, Candida kefyr, Candida tropicalis, and Candida parapsilosis. Microbiological analysis showed that all new thiazolidinone derivatives with nitronaphthylamine substituent possessed antibacterial and antifungal properties. New compounds 2a-b showed similar antibacterial activity in vitro against S. aureus and B. subtilis as aminopenicillins. The lowest antibacterial activity of all newly synthesized compounds was against capsule-forming bacteria K. pneumoniae and against gram-negative bacteria E. coli (minimum inhibitory concentration range, 500-1000 μg/mL). The minimum inhibitory concentration of naphthylamine derivatives varied in the range of 0.4-1000 μg/mL, and activity of some newly synthesized compounds was similar to the activity of aminopenicillins and fluconazole, an antifungal preparation. Based on the results, it is possible to separate the perspective group of potential antimicrobial compounds.
Highlights
The incidence of fungal infections has increased over the last two decades, and Candida spp. have been reported as predominant mycotic pathogens [1]
Microbiological analysis showed that all new thiazolidinone derivatives with nitronaphthylamine substituent possessed antibacterial and antifungal properties
The minimum inhibitory concentration of naphthylamine derivatives varied in the range of 0.4–1000 μg/mL, and activity of some newly synthesized compounds was similar to the activity of aminopenicillins and fluconazole, an antifungal preparation
Summary
The incidence of fungal infections has increased over the last two decades, and Candida spp. have been reported as predominant mycotic pathogens [1]. For a number of years, the Department of Drug Chemistry, the Lithuanian University of Health Sciences, has investigated new thiazolidinone derivatives, which are obtained by substituting the second position with an amine moiety, such as sulfanilamides or other amines, which have antimicrobial pharmacophores [9,10,11]. The selection of such antimicrobial pharmacophores was determined by our idea to investigate new compounds that have advantages vis-à-vis initial products. Search for a more potent antibacterial alternative is still a challenge
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