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Antimicrobial properties of 3-(2-methylfuran-3-yl)- 4-substituted-Δ2-1,2,4-triazoline-5-thiones

Agata Siwek 1Joanna Stefańska 2Nazar Trotsko 1Monika Wujec 1

1. Medical University, Staszica 6, Lublin 20081, Poland
2. Medical University of Warsaw, Department of Pharmaceutical Microbiology, Oczki, Warsaw 02-007, Poland

Abstract

The biological activities of 1,2,4-triazoles have been extensively studied. In particular, their antimicrobial and CNS activities have been extensively documented. Although limited, there are also examples of the antibacterial, antinociceptive, anti-inflammatory properties of furan derivatives We have hypothesized that 3-(2-methylfuran-3-yl)-4-substituted- Δ2-1,2,4-triazoline-5-thiones might show antimicrobial and antifungal activity. To test this hypothesis we have synthesized four new analogous with phenyl, 2/4-tolyl, 4-methoxyphenyl and cyclohexyl substituents in the position 4 of 1,2,4-triazoline-5-thione.

The assessment of the antimicrobial action of the synthesized compounds was performed using the disc-diffusion method and the minimal inhibitory concentration (MIC). Minimum inhibitory concentrations (MICs) were defined as the lowest concentration of the compounds that inhibited visible growth of microorganisms after 18 h incubation at 35°C. Microorganisms used in this study were as fallows: Gram-positive bacteria: four strains of Staphylococcus aureus (NCTC 4163, ATCC 25923, ATCC 6538, ATCC 2921), Staphylococcus epidermidis ATCC 12228, Bacillus subtilis ATCC 6633, Bacillus cereus ATCC 11778, Enterococcus hirae ATCC 10541, Micrococcus luteus ATCC 9341, Micrococcus luteus ATCC 10240 and Gram-negative rods: three strains of Escherichia coli (ATCC 10538, ATCC 25922, NCTC 8196), Proteus vulgaris NCTC 4635, three strains of Pseudomonas aeruginosa (ATCC 15442, NCTC 6749, ATCC 27863), Bordetella bronchiseptica ATCC 4617. For testing antifungal activities of the compounds, fallowing reference strains were tested: Candida albicans ATCC 10231, Candida albicans ATCC 90028 and Candida parapsilosis ATCC 22019. The results revealed that all tested compounds were inactive against all tested yeasts. 4-(2-Tolyl)-3-(2-methyl-furan-3-yl)-Δ2-1,2,4-triazoline-5-thiones exhibited activity against Gram-positive bacteria, especially against M. luteus ATCC 9341 (MIC 50 µg/ml).

 

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Submitted: 2008-03-13 12:46
Revised:   2009-06-07 00:48