Nucleic acid component analogues: design and direct route to novel 2-( <i>β-L</i> -arabino- and <i>β-D-</i> xylopyranosylthio)pyridine glycosides as potential antimicrobial agents

The sodium salts of 2-formyl-1-cycloalkanones and α-(hydroxymethylene)alkanones, when reacted with cyanothioacetamide, produced equivalent cycloalkane ring fused pyridine-2(1<i>H</i>)-thiones and substituted pyridone-2(1<i>H</i>)-thiones. The corresponding pyridine S-glycosides were obtained in good yields from the later compounds by a successful coupling reaction with protected bromoarabinose or bromoxylose in KOH-acetone at room temperature and/or HDMS/(NH₄)₂SO₄. After ten minutes of room temperature reaction between the later compounds and NH₃-MeOH, excellent yields of the deprotected derivatives were produced. Using spectral data and fundamental analyses, the structure of the newly synthesized compounds were proved (IR, ¹H NMR, and ¹³C NMR). All prepared thioglycoside substances had their antibacterial properties assessed and screened. Some thioglycoside derivatives turned out to be potent antibacterial agents.