Synthesis and antimicrobial activity of sulphamethoxazole-based ureas and imidazolidine-2,4,5-triones
-
Martin Krátký
,
Jana Mandíková
Abstract
Progression of drug resistance among bacterial and fungal pathogens justifies the development of novel antimicrobial agents. Thus, a series of novel sulphamethoxazole-based ureas and imidazolidine- 2,4,5-triones have been designed and synthesised. The urea derivatives were obtained by the reaction of sulphamethoxazole and isocyanates, and their cyclisation to imidazolidine-2,4,5-triones was performed via oxalyl chloride. All synthesised derivatives were evaluated in vitro to determine their activity against gram-positive and gram-negative bacteria, fungi, Mycobacterium tuberculosis, and atypical mycobacteria and their cytotoxicity. The growth of mycobacteria was inhibited within the range of 4-1000 μM and M. tuberculosis was the least-susceptible strain. 4-(3-Heptylureido)- N-(5-methylisoxazol-3-yl)benzenesulphonamide was identified as the most promising compound because it exhibited the highest activity against atypical mycobacteria at minimum inhibitory concentrations, from 4 μM, and with acceptable toxicity (selectivity indices for M. avium and M. kansasii higher than 16 and 62.5, respectively). Gram-positive bacteria, including methicillinresistant Staphylococcus aureus, were inhibited at concentrations starting from 125 μM, whereas the investigated derivatives exhibited almost no antifungal potency and activity against gram-negative species.
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Articles in the same Issue
- Deferoxamine–paper for iron(III) and vanadium(V) sensing
- Integrated investigations for the characterisation of Roman lead-glazed pottery from Pompeii and Herculaneum (Italy)
- Determination of acetylcholinesterase and butyrylcholinesterase activity without dilution of biological samples
- Characterization of a novel Aspergillus niger beta-glucosidase tolerant to saccharification of lignocellulosic biomass products and fermentation inhibitors
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- Antimicrobial properties and chemical composition of liquid and gaseous phases of essential oils
- Syntheses, structures and properties of isonicotinamidium, thionicotinamidium, 2- and 3-(hydroxymethyl)pyridinium nitrates
- Density of lithium fluoride–lithium carbonate-based molten salts
- Synthesis and antimicrobial activity of sulphamethoxazole-based ureas and imidazolidine-2,4,5-triones
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