Lozynskyi Andrii, Zasidko Viktoria, Atamanyuk Dmytro, Kaminskyy Danylo, Derkach Halyna, Karpenko Olexandr, Ogurtsov Volodymyr, Kutsyk Roman, Lesyk Roman
Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, 69 Pekarska, Lviv, 79010, Ukraine.
Department of Microbiology, Virology and Immunology, Ivano-Frankivsk National Medical University, 2 Halytska, Ivano-Frankivsk, 76018, Ukraine.
Mol Divers. 2017 May;21(2):427-436. doi: 10.1007/s11030-017-9737-8. Epub 2017 Apr 19.
Here it is described the synthesis, antioxidant and antimicrobial activity determination of novel rel-([Formula: see text])-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 [Formula: see text]-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 [Formula: see text]), but slight effect on Escherichia coli.
本文描述了新型rel-([化学式：见原文])-6-苯甲酰基-7-苯基-2-氧代-3,5,6,7-四氢-2H-硫代吡喃并[2,3-d]噻唑-5-羧酸的合成、抗氧化和抗菌活性测定。通过区域和非对映选择性杂环狄尔斯-阿尔德反应，从5-亚芳基-4-硫代-2-噻唑烷酮和[化学式：见原文]-芳酰基丙烯酸以良好的产率获得了目标化合物。环加成的立体化学通过核磁共振光谱得到证实。抗氧化和抗菌活性筛选鉴定出7种化合物（3c、3e、3f、3g、3k、3l、3p）具有高水平的自由基清除能力（43 - 77% DPPH测定法），以及对金黄色葡萄球菌、枯草芽孢杆菌和白色念珠菌有显著影响的化合物（最低抑菌浓度3.13 - 6.25 [化学式：见原文]），但对大肠杆菌的影响较小。
