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Molecular Diversity

, Volume 21, Issue 2, pp 427–436 | Cite as

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

  • Andrii Lozynskyi
  • Viktoria Zasidko
  • Dmytro Atamanyuk
  • Danylo Kaminskyy
  • Halyna Derkach
  • Olexandr Karpenko
  • Volodymyr Ogurtsov
  • Roman Kutsyk
  • Roman LesykEmail author
Original Article

Abstract

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 \(\upbeta \)-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 \(\upmu \hbox {g/mL}\)), but slight effect on Escherichia coli.

Graphical abstract

Keywords

Hetero-Diels–Alder reaction Thiopyrano[2,3-d]thiazoles Antioxidant activity Antimicrobial activity 

Supplementary material

11030_2017_9737_MOESM1_ESM.docx (2.1 mb)
Supplementary material 1 (docx 2140 KB)

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Copyright information

© Springer International Publishing Switzerland 2017

Authors and Affiliations

  1. 1.Department of Pharmaceutical, Organic and Bioorganic ChemistryDanylo Halytsky Lviv National Medical UniversityLvivUkraine
  2. 2.Department of Microbiology, Virology and ImmunologyIvano-Frankivsk National Medical UniversityIvano-FrankivskUkraine
  3. 3.Department of ChemistryIvano-Frankivsk National Medical UniversityIvano-FrankivskUkraine
  4. 4.Enamine Ltd.KievUkraine
  5. 5.Department of General, Bioinorganic, Physical and Colloidal ChemistryDanylo Halytsky Lviv National Medical UniversityLvivUkraine

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