Synthesis and In Vitro Anti-Helicobacter and Anti-Staphylococcal Activities of Novel Diaryldisulfides and Diarylthiosulfonates

Arylthiols were reacted with acrylonitrile under basic conditions to form the corresponding aryl sulfides which were oxidised with sodium metaperiodate in aqueous methanol to yield 3-arylsulphinylpropanenitriles that upon thermolysis in refluxing toluene produced a mixture of diarylthiosulfonates and diaryldisulfides. The mixture of the two products was easily separated by flash chromatography and characterized spectroscopically. The diarylthiosulfonates and diaryldisulfides, garlic-like organosulfur compounds, were tested for their antimicrobial properties against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Helicobacter pylori and had been found to have good activity against S. aureas and H. pylori with no activity against the other two organisms.