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Molecules 2014, 19(9), 13704-13723; https://doi.org/10.3390/molecules190913704

Synthesis and Anti-Yeast Evaluation of Novel 2-Alkylthio-4-chloro-5-methyl-N-[imino-(1-oxo-(1H)-phthalazin-2-yl)methyl]benzenesulfonamide Derivatives

1
Department of Organic Chemistry, Medical University of Gdańsk, Al. Gen. J. Hallera 107, Gdańsk 80-416, Poland
2
Department of Oral Microbiology, Medical University of Gdańsk, ul. Do Studzienki 38, Gdańsk 80-227, Poland
*
Author to whom correspondence should be addressed.
Received: 11 July 2014 / Revised: 13 August 2014 / Accepted: 25 August 2014 / Published: 2 September 2014
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Pathogenic fungi are one of the main causes of hospital-related infections. Since conventional antifungals have become less effective because of the increasing fungal resistance to the standard drugs, the need for new agents is becoming urgent. Herein we report a synthesis of a series of novel N-[imino-(1-oxo-(1H)-phthalazin-2-yl)methyl]-benzenesulfonamide derivatives with in vitro activity against yeast-like fungi isolated from the oral cavity and respiratory tract of patients with candidiasis. These compounds were synthesized by the one-step or two-step reactions of 1-(2-alkylthiobenzensulfonyl)-2-aminoguanidines with the appropriate ortho-carbonyl benzoic acids. The biological study revealed that new derivatives have shown significant growth-inhibitory activity, superior or comparable, than those of the reference drug fluconazole. The most promising activities were observed against Candida albicans, with inhibition at least 1–3 (12.5%–37.5%) of the eight tested strains at the low MIC level of ≤6.2–25 µg/mL. View Full-Text
Keywords: sulfonamides; phthalazine; antifungal agents; structure-activity relationship; Candida sulfonamides; phthalazine; antifungal agents; structure-activity relationship; Candida
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Sławiński, J.; Pogorzelska, A.; Żołnowska, B.; Kędzia, A.; Ziółkowska-Klinkosz, M.; Kwapisz, E. Synthesis and Anti-Yeast Evaluation of Novel 2-Alkylthio-4-chloro-5-methyl-N-[imino-(1-oxo-(1H)-phthalazin-2-yl)methyl]benzenesulfonamide Derivatives. Molecules 2014, 19, 13704-13723.

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