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

• Published in: Molecular diversity 2017-05, Vol.21 (2), p.427-436
• Main Authors: Lozynskyi, Andrii, Zasidko, Viktoria, Atamanyuk, Dmytro, Kaminskyy, Danylo, Derkach, Halyna, Karpenko, Olexandr, Ogurtsov, Volodymyr, Kutsyk, Roman, Lesyk, Roman
• Format: Article
• Language: English
• Subjects: Acrylates - chemistry; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; Antifungal agents; Antimicrobial agents; Antioxidants; Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; Bacteria - drug effects; Biochemistry; Biomedical and Life Sciences; Candida albicans - drug effects; Chemical compounds; Chemical synthesis; Chemistry; Chemistry Techniques, Synthetic; Life Sciences; Organic Chemistry; Original Article; Pharmacy; Polymer Sciences; Structure-Activity Relationship; Thiazoles - chemical synthesis; Thiazoles - chemistry; Thiazoles - pharmacology
• ISSN: 1381-1991; 1573-501X
• DOI: 10.1007/s11030-017-9737-8

Here it is described the synthesis, antioxidant and antimicrobial activity determination of novel rel- ( 5 R , 6 S , 7 R )-6-benzoyl-7-phenyl-2-oxo-3,5,6,7-tetrahydro-2 H -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 μ g/mL ), but slight effect on Escherichia coli . Graphical abstract