Oxidation of 4,6-dimethyl-2-thioxo-1,2-dihydropyridine3-carbonitriles with potassium hexacyanoferrate(III): synthesis and molecular docking of bis(pyrid-2-yl)disulfides

Abstract

The reaction of 4,6-dimethyl-2-thioxo-1,2-dihydropyridin-3-carbonitriles with K3[Fe(CN)6] in an alkaline medium led to the formation of a mixture of oxidation products: bis(3-cyanopyridin-2-yl)disulfides and potassium 3-cyano-4,6-dimethylpyridine-2-sulfonates. Structure of the compounds was confirmed by NMR, IR spectroscopy and high-resolution mass spectrometry data. According to the results of molecular docking, 2,2′-dithiobis(5-butyl-4,6-dimethylnicotinonitrile) exhibits affinity for the zinc finger binding site of the HIV-1 p7 nucleocapsid protein.