Synthesis, structure, and antiviral activity 4(6)-β-d-glucopyranosylamino-2-R-1,3-benzothiazoles

A one-step stereoselective synthesis of β-N-benzothiazolyl glycosides was developed by glycosylation of amino-2-pentafluorosulfanyl-1,3-benzothiazole and amino-2-trifluoromethyl-1,3-benzothiazole derivatives using unprotected d-glucose in ethanol solution. The structure of β-N-glycosides was confirmed by X-ray crystallography. Starting 4- and 6-amino substituted benzothiazoles bearing pentafluorosufanyl and trifluoromethyl groups were prepared from the corresponding nitro derivatives by the reduction with iron in NH₄Cl/H₂O media. The pKa values of the new aminobenzothiazoles were determined by potentiometric acid-base titration. Cytotoxicity in MDCK and Wish cell cultures was determined to evaluate the biological activity of the new compounds, and the antiviral activity against influenza virus type A (H1N1) was investigated. It was shown that 4-β-d-glucopyranosylamino-2-(trifluoromethyl)-1,3-benzothiazole shoved the ability to inhibit virus reproduction in cells.