Synthesis and antimicrobial activity of sulphamethoxazole-based ureas and imidazolidine-2,4,5-triones
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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.
References
Agertt, V. A., Marques, L. L., Bonez, P. C., Dalmolin, T. V., Manzoni de Oliveira, G. N., & Anraku de Campos, M. M. (2013). Evaluation of antimycobacterial activity of a sulphonamide derivative. Tuberculosis, 93, 318-321. DOI: 10.1016/j.tube.2013.02.003.10.1016/j.tube.2013.02.003Suche in Google Scholar PubMed
Akgün, H., Karamelekoğlu, I., Berk, B., Kurnaz, I., Sarıbıyık, G., Öktem, S., & Kocagöz, T. (2012). Synthesis and antimycobacterial activity of some phthalimide derivatives. Bioorganic & Medicinal Chemistry, 20, 4149-4154. DOI: 10.1016/j.bmc.2012.04.060.10.1016/j.bmc.2012.04.060Suche in Google Scholar PubMed
Alsaad, N., van der Laan, T., van Altena, R.,Wilting, K. R., van der Werf, T. S., Stienstra, Y., van Soolingen, D., & Alffenaar, J. W. C. (2013). Trimethoprim/sulfamethoxazole susceptibility of Mycobacterium tuberculosis. International Journal of Antimicrobial Agents, 42, 472-474. DOI: 10.1016/j.ijantimicag.2013.07.011.10.1016/j.ijantimicag.2013.07.011Suche in Google Scholar PubMed
Ameen, S. M., & Drancourt, M. (2013). In vitro susceptibility of Mycobacterium avium complex mycobacteria to trimethoprim and sulphonamides. International Journal of Antimicrobial Agents, 42, 281-282. DOI: 10.1016/j.ijantimicag.2013.05.006.10.1016/j.ijantimicag.2013.05.006Suche in Google Scholar PubMed
Brown, J. R., North, E. J., Hurdle, J. G., Morisseau, C., Scarborough, J. S., Sun, D., Kordulakova, J., Scherman, M. S., Jones, V., Grzegorzewicz, A., Crew, R. M., Jackson, M., Mc-Neil, M. R., & Lee, R. E. (2011). The structure-activity relationship of urea derivatives as anti-tuberculosis agents. Bioorganic & Medicinal Chemistry, 19, 5585-5595. DOI: 10.1016/j.bmc.2011.07.034.10.1016/j.bmc.2011.07.034Suche in Google Scholar PubMed PubMed Central
Desai, S. R., Laddi, U., Bennur, R. S., Patil, P. A., & Bennur, S. (2011). Synthesis and pharmacological activities of some new 5-substituted-2-mercapto-1,3,4-oxadiazoles. Indian Journal of Pharmaceutical Sciences, 73, 593-596. DOI: 10.4103/0250-474x.99025.10.4103/0250-474X.99025Suche in Google Scholar PubMed PubMed Central
Huang, T. S., Kunin,C.M., Yan, B. S.,Chen, Y. S., Lee, S. S. J., & Syu, W. J. (2012). Susceptibility of Mycobacterium tuberculosis to sulfamethoxazole, trimethoprim and their combination over a 12 year period in Taiwan. Journal of Antimicrobial Chemotherapy, 67, 633-637. DOI: 10.1093/jac/dkr501.10.1093/jac/dkr501Suche in Google Scholar PubMed
Kratky, M., & Vinšova, J. (2012). Antifungal activity of salicylanilides and their esters with 4-(trifluoromethyl)benzoic acid. Molecules, 17, 9426-9442. DOI: 10.3390/molecules17089426.10.3390/molecules17089426Suche in Google Scholar PubMed PubMed Central
Kratky, M., Vinšova, J., Volkova, M., Buchta, V., Trejtnar, F., & Stolařikova, J. (2012). Antimicrobial activity of sulfonamides containing 5-chloro-2-hydroxybenzaldehyde and 5-chloro-2-hydroxybenzoic acid scaffold. European Journal of Medicinal Chemistry, 50, 433-440. DOI: 10.1016/j.ejmech.2012.01.060.10.1016/j.ejmech.2012.01.060Suche in Google Scholar PubMed
Kratky, M., Vinšova, J., Novotna, E., Mandikova, J., Trejtnar, F., & Stolařikova, J. (2013). Antibacterial activity of salicylanilide 4-(trifluoromethyl)benzoates. Molecules, 18, 3674-3688. DOI: 10.3390/molecules18043674.10.3390/molecules18043674Suche in Google Scholar PubMed PubMed Central
Maresca, A., Scozzafava, A., Vullo, D., & Supuran, C. T. (2013). Dihalogenated sulfanilamides and benzolamides are effective inhibitors of the three β-class carbonic anhydrases from Mycobacterium tuberculosis. Journal of Enzyme Inhibition and Medicinal Chemistry, 28, 384-387. DOI: 10.3109/14756366.2011.645539.10.3109/14756366.2011.645539Suche in Google Scholar PubMed
Minakuchi, T., Nishimori, I., Vullo, D., Scozzafava, A., & Supuran, C. T. (2009). Molecular cloning, characterization, and inhibition studies of the Rv1284 β-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate. Journal of Medicinal Chemistry, 52, 2226-2232. DOI: 10.1021/jm9000488.10.1021/jm9000488Suche in Google Scholar PubMed
North, E. J., Scherman, M. S., Bruhn, D. F., Scarborough, J. S., Maddox, M. M., Jones, V., Grzegorzewicz, A., Yang, L., Hess, T., Morisseau, C., Jackson, M., McNeil, M. R., & Lee, R. E. (2013). Design, synthesis and anti-tuberculosis activity of 1-adamantyl-3-heteroaryl ureas with improved in vitro pharmacokinetic properties. Bioorganic & Medicinal Chemistry, 21, 2587-2599. DOI: 10.1016/j.bmc.2013.02.028.10.1016/j.bmc.2013.02.028Suche in Google Scholar PubMed PubMed Central
Pejchal, V., Stepankova, S., Padelkova, Z., Imramovsky, A., & Jampilek, J. (2011). 1,3-Substituted imidazolidine-2,4,5-triones: Synthesis and inhibition of cholinergic enzymes. Molecules, 16, 7565-7582. DOI: 10.3390/molecules16097565.10.3390/molecules16097565Suche in Google Scholar PubMed PubMed Central
Sukdolak, S., Solujić, S., Manojlović, N., & Krstić, L. J. (2005). Synthesis and antimicrobial activity of new N-[4-(4-hydroxy- 2-oxo-2H-chromen-3-yl)thiazol-2-yl]benzenesulfonamides. Chemical Papers, 59, 37-40.Suche in Google Scholar
Thomas, K. D., Adhikari, A. V., Chowdhury, I. H., Sumesh, E., & Pal, N. K. (2011). New quinolin-4-yl-1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines as potential antitubercular agents. European Journal of Medicinal Chemistry, 46, 2503-2512. DOI: 10.1016/j.ejmech.2011.03.039.10.1016/j.ejmech.2011.03.039Suche in Google Scholar PubMed
Yun, M. K., Wu, Y., Li, Z., Zhao, Y., Waddell, M. B., Ferreira, A. M., Lee, R. E., Bashford, D., & White, S. W. (2012). Catalysis and sulfa drug resistance in dihydropteroate synthase. Science, 335, 1110-1114. DOI: 10.1126/science.1214641. 10.1126/science.1214641Suche in Google Scholar PubMed PubMed Central
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- 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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