Collect. Czech. Chem. Commun. 1985, 50, 375-382

Structure characterization of reaction products from phenylhydrazonopropanedinitrile and thiols

Pavol Suloa, Ernest Šturdíka, Tibor Liptajb, Tibor Jakubíkc and Marián Antalíkd

a Department of Technical Microbiology and Biochemistry
b Department of Physical Chemistry
c Laboratory of Mass Spectrometry, Faculty of Chemical Technology, Slovak Technical University, 812 37 Bratislava
d Institute of Neurobiology, Centre of Physiological Sciences, Slovak Academy of Sciences, 040 11 Košice


Phenylhydrazonopropanedinitriles react with thiols (benzyl mercaptan, cysteine, 2-mercaptoethanol, mercaptoacetic acid, glutathione, and alcohol dehydrogenase) to give addition products in which thiolate anion is attached to electrophilic carbon atom of cyano group. The reaction ability and way of reaction of phenylhydrazonopropanedinitriles are discussed in the context of mechanism of biological activity of these compounds, particularly that of their uncoupling effect on oxidative phosphorylation.