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Molecules 2017, 22(4), 535; doi:10.3390/molecules22040535

Novel Sulfamethoxazole Ureas and Oxalamide as Potential Antimycobacterial Agents

1
Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Heyrovského 1203, 50005 Hradec Králové, Czech Republic
2
Laboratory for Mycobacterial Diagnostics and Tuberculosis, Regional Institute of Public Health in Ostrava, Partyzánské námĕstí 7, 70200 Ostrava, Czech Republic
*
Author to whom correspondence should be addressed.
Academic Editor: Claudiu T. Supuran
Received: 2 March 2017 / Revised: 23 March 2017 / Accepted: 24 March 2017 / Published: 28 March 2017
(This article belongs to the Special Issue Sulfonamides)
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Abstract

Infections caused by Mycobacterium tuberculosis (Mtb.) and nontuberculous mycobacteria (NTM) are considered to be a global health problem; current therapeutic options are limited. Sulfonamides have exhibited a wide range of biological activities including those against mycobacteria. Based on the activity of 4-(3-heptylureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide against NTM, we designed a series of homologous sulfamethoxazole-based n-alkyl ureas (C1–C12), as well as several related ureas and an oxalamide. Fifteen ureas and one oxalamide were synthesized by five synthetic procedures and characterized. They were screened for their activity against Mtb. and three NTM strains (M. avium, M. kansasii). All of them share antimycobacterial properties with minimum inhibitory concentration (MIC) values starting from 2 µM. The highest activity showed 4,4′-[carbonylbis(azanediyl)]bis[N-(5-methylisoxazol-3-yl)benzenesulfonamide] with MIC of 2–62.5 µM (i.e., 1.07–33.28 µg/mL). Among n-alkyl ureas, methyl group is optimal for the inhibition of both Mtb. and NTM. Generally, longer alkyls led to increased MIC values, heptyl being an exception for NTM. Some of the novel derivatives are superior to parent sulfamethoxazole. Several urea and oxalamide derivatives are promising antimycobacterial agents with low micromolar MIC values. View Full-Text
Keywords: antimycobacterial activity; in vitro activity; oxalamide; sulfamethoxazole; sulfonamides; tuberculosis; ureas antimycobacterial activity; in vitro activity; oxalamide; sulfamethoxazole; sulfonamides; tuberculosis; ureas
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Krátký, M.; Stolaříková, J.; Vinšová, J. Novel Sulfamethoxazole Ureas and Oxalamide as Potential Antimycobacterial Agents. Molecules 2017, 22, 535.

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