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Medicina is published by MDPI from Volume 54 Issue 1 (2018). Articles in this Issue were published by another publisher in Open Access under a CC-BY (or CC-BY-NC-ND) licence. Articles are hosted by MDPI on mdpi.com as a courtesy and upon agreement with Lithuanian Medical Association, Lithuanian University of Health Sciences, and Vilnius University.
Open AccessArticle

Synthesis and Antimicrobial Properties of Naphthylamine Derivatives Having a Thiazolidinone Moiety

1
Department of Drug Chemistry, Medical Academy, Lithuanian University of Health Sciences
2
Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University
3
Department of Microbiology, Medical Academy, Lithuanian University of Health Sciences, Lithuania
*
Author to whom correspondence should be addressed.
Medicina 2011, 47(6), 47; https://doi.org/10.3390/medicina47060047
Received: 1 October 2010 / Accepted: 23 June 2011 / Published: 28 June 2011
Objective. 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.
Materials and Methods
. 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.
Results
. 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).
Conclusions
. 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.
Keywords: antifungal activity; antimicrobial activity; naphthylamine; nitrofurans; thiazolidinone; synthesis of new drugs antifungal activity; antimicrobial activity; naphthylamine; nitrofurans; thiazolidinone; synthesis of new drugs
MDPI and ACS Style

Petrikaitė, V.; Tarasevičius, E.; Pavilonis, A. Synthesis and Antimicrobial Properties of Naphthylamine Derivatives Having a Thiazolidinone Moiety. Medicina 2011, 47, 47.

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