5-Ene-rhodanine-3-carboxylic acids as potential antimicrobial and antiparasitic agents

Aim. Design, synthesis and study of antibacterial, antifungal and trypanocidal activity of a series of novel 2-thioxo-4-thiazolidinone-3-carboxylic acids with different arylidene substituents in C5 position. Methods: organic wet synthesis, analytical and spectral methods, pharmacological screening,...

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Bibliographic Details
Published in:Biopolimery i kletka 2020, Vol.36 (3), p.229-241
Main Author: Kryshchyshyn-Dylevych, A. P.
Format: Article
Language:English
Subjects:
Acids
Amines
Ammonium
Antifungal activity
Antifungal agents
Antiparasitic agents
Candida
Candida albicans
Carboxylic acids
Cytotoxicity
Fibroblasts
Gram-negative bacteria
Pyridines
Staphylococcus
Strains (organisms)
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Summary:Aim. Design, synthesis and study of antibacterial, antifungal and trypanocidal activity of a series of novel 2-thioxo-4-thiazolidinone-3-carboxylic acids with different arylidene substituents in C5 position. Methods: organic wet synthesis, analytical and spectral methods, pharmacological screening, SAR analysis. Results. A series of 5-(aminomethylene)-4-oxo-2-thioxothiazolidin-3-ylcarboxylic acids and their analogs IIIa-IIIj were synthesized in the reactions of 5-(ethoxymethylene)-4-oxo-2-thioxothiazolidin-3-ylcarboxylic acids IIa,b or ethyl 5-(ethoxymethylene)-4-oxo-2-thioxothiazolidin-3-ylpropanoate IIc with various amines and ammonium hydrogen carbonate. Five of the synthesized compounds IIIb, IIIf and IIIh-j were tested towards a series of Gram (+) and Gram (–) bacteria and four yeasts strains at a dose of 1mM. In general, [the] tested compounds are promising building scaffolds for the development of antifungal agents as all of them inhibited growth of clinical strain of Candida albicans. Moreover, pyridine containing 3-[5-(aminomethylene)-rhodanine-3-yl]carboxylates showed good trypanocidal activity and low cytotoxicity towards normal fibroblasts. Conclusions. A series of novel 3-[5-(aminomethylene)-4-oxo-2-thioxothiazolidin-3-yl]carboxylic acids derivatives were synthesized. Study of their antibacterial and antifungal action allowed identifying a hit-compound ethyl 3-[5-[(4-(fluoroanilino)methylene]-4-oxo-2-thioxothiazolidin-3-yl]propanoate IIIf, which is active against clinical strains of Staphylococcus lentus and Candida ssp. In general, most of the studied compounds showed good antifungal properties.
ISSN:0233-7657
1993-6842
DOI:10.7124/bc.000A2F