In search for effective inhibitors of sugar processing enzymes the S-glycosides and products of their oxidation attract constant attention as viable substrate analogs.

Along this line, we have reported a simple and efficient methodology for the synthesis of thioglycosides, derivatives of nitroaromatic halides, via aromatic nucleophilic substitution of halogen with 1-thiosugar derivatives [1,2]. Phenyl thioglycosides used in our study were prepared as described in literature, in reaction of acylglycosyl halides with thiophenol under phase transfer conditions [3].

The oxidation of glycosyl sulfides respectively to sulfoxides or sulfones was achieved using common oxidising agent [4]: m-chloroperbenzoic acid (m-CPBA) in CH₂Cl₂ at room temperature. During oxidation to sulfoxides m-CPBA was added in equimolar amount in low temperature (-20 ^oC) to avoid sulfone formation.

Desired oxidation products were obtained in a good yield and their structures were confirmed by NMR spectra.

Biological studies with these inhibitors were divided into two parts. First, using the neutral red cytotoxicity assay, we established the optimal doses of inhibitors when the viability of swine kidney cells (SK6) was higher than 50%. In the next experiments, we examined the effect of concentration of inhibitors on penetration and propagation of classical swine fever virus (CSFV). The best results were observed for GP5 inhibitor. Even low doses of this inhibitor (5 μg/ml), when the viability of SK6 cells is higher than 90%, inhibited the propagation of CSFV virus and the viral yield was decreased by over 70%.

1. H. Driguez, W. Szeja, Synthesis, 1994, 14132.
2. G. Pastuch, W. Szeja, Carbohydr. Lett., 1997, 2, 2813.
3. B. Yeung, D. Hill, M. Janicka, P. Petillo, Org. Lett., 2000, 9, 1279
4. 4. D. Kahne, S. Walker, Y. Cheng, D. Van Engen, J. Am. Chem. Soc., 1989, 111, 6881.

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