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Synthesis, antioxidant and antimicrobial activities of novel thiopyrano[2,3-d]thiazoles based on aroylacrylic acids

Mol. Diver. 2017, 21 (2), 427-436

DOI: 10.1007/s11030-017-9737-8

Lozynskyi A.; Zasidko V.; Atamanyuk D.; Kaminskyy D.; Derkach H.; Karpenko O.; Ogurtsov V.; Kutsyk R.; Lesyk R.
Here it is described the synthesis, antioxidant and antimicrobial activity determination of novel rel-(5R,6S,7R)-6-benzoyl-7-phenyl-2-oxo-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazole-5-carboxylic acids. The target compounds were obtained in good yields from 5-arylidene-4-thioxo-2-thiazolidinones and β-aroylacrylic acids via regio- and diastereoselective hetero-Diels–Alder reaction. The stereochemistry of the cycloaddition was confirmed by NMR spectra. The antioxidant and antimicrobial activity screening identified 7 compounds (3c, 3e, 3f, 3g, 3k, 3l, 3p) with a high level of free radical scavenging (43–77% DPPH assay), and compounds with significant influence on Staphylococcus aureus, Bacillus subtilis and Candida albicans (MIC 3.13–6.25 μg/mL), but slight effect on Escherichia coli.

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