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Molecules 2017, 22(11), 1926; doi:10.3390/molecules22111926

Syntheses of Novel 4-Substituted N-(5-amino-1H-1,2,4-triazol-3-yl)pyridine-3-sulfonamide Derivatives with Potential Antifungal Activity

1
Department of Organic Chemistry, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland
2
Department of Oral Microbiology, Medical University of Gdańsk, ul. Dębowa 25., 80-204, Gdańsk, Poland
*
Authors to whom correspondence should be addressed.
Received: 10 October 2017 / Revised: 2 November 2017 / Accepted: 3 November 2017 / Published: 7 November 2017
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Abstract

Candidiasis represent a serious threat for patients with altered immune responses. Therefore, we have undertaken the synthesis of compounds comprising a pyridine-3-sulfonamide scaffold and known antifungally active 1,2,4-triazole substituents. Thus a series of novel 4-substituted N-(5-amino-1H-1,2,4-triazol-3-yl)pyridine-3-sulfonamides have been synthesized by multistep reactions starting from 4-chloropyridine-3-sulfonamide via N′-cyano-N-[(4-substitutedpyridin-3-yl)sulfonyl]carbamimidothioates which were further converted with hydrazine hydrate to the corresponding 1,2,4-triazole derivatives 2636. The final compounds were evaluated for antifungal activity against strains of the genera Candida, Geotrichum, Rhodotorula, and Saccharomycess isolated from patients with mycosis. Many of them show greater efficacy than fluconazole, mostly towards Candida albicans and Rhodotorula mucilaginosa species, with MIC values ≤ 25 µg/mL. A docking study of the most active compounds 26, 34 and 35 was performed showing the potential mode of binding to Candida albicans lanosterol 14α-demethylase. Also in vitro cytotoxicity of selected compounds have been evaluated on the NCI-60 cell line panel. View Full-Text
Keywords: sulfonamides; pyridine-3-sulfonamides; 1,2,4-triazole; antifungal agents; Candida albicans; anticancer screening sulfonamides; pyridine-3-sulfonamides; 1,2,4-triazole; antifungal agents; Candida albicans; anticancer screening
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Szafrański, K.; Sławiński, J.; Kędzia, A.; Kwapisz, E. Syntheses of Novel 4-Substituted N-(5-amino-1H-1,2,4-triazol-3-yl)pyridine-3-sulfonamide Derivatives with Potential Antifungal Activity. Molecules 2017, 22, 1926.

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