Synthesis and study of the antioxidant activity of sulfur-containing 3,7-diazabicyclononanes

By reaction of 1,5-dialkl-9-oxo-3,7-diazabicyclo/3.3.1/nonane with phenylisothiocyanate synthesized the corresponding 3,7-disubstituted phenylisothiocyanates.The above bicyclononane is converted with cyanoacetic acid methyl ester to a monocyano derivative which, with substituted phenylisothiocyanates, forms the 3,7-disubstituted 1,5-dialkyl-9-oxo-3,7-diazabicyclo/3.3.1/nonanes. From 5,7-dialkyl-6-oxo-1,3-dia-zaadamantane, 1,5-dialkyl-3-methyl-9-hydroxy-3,7-diazabicyclo/3.3.1/nonane was synthesized, which was converted by reaction with substituted benzoylisothiocyanates to 3,7-disubstituted bicyclononanes. The corresponding 3,7-disulfo derivatives of 1,5-dialkyl-9-oxo-3,7-diazabicyclo-/3.3.1/nonanes were synthesized by the reaction of 5,7-dialkyl-6-oxo-1,3-dia-diazaadamantane with benzenesulfochloride. According to the results of biological tests, some derivatives of this series have moderate antioxidant activity, especially compounds, containga hydroxyl group in 9-th position of diazabicyclononane