Biopolym. Cell. 2020; 36(3):229-241.
Bioorganic Chemistry
5-Ene-rhodanine-3-carboxylic acids as potential antimicrobial and antiparasitic agents
1Kryshchyshyn-Dylevych A. P.
  1. Danylo Halytsky Lviv National Medical University
    69, Pekarska Str., Lviv, Ukraine, 79010


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.
Keywords: 2-thioxo-4-thiazolidinone-3-carboxylic acids, rhodanine, synthesis, antitrypanosomal activity, antibacterial activity, antifungal activity, SAR


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