Synthesis and antioxidant activity of 3-(2-R-ylidenehydrazinyl)-6-tert-butyl-4H-[1,2,4]triazin-5-ones

Abstract

Synthesis and structure elucidation of several series of new hydrazones containing 1,2,4-triazine-5-one core and their antioxidant activity are presented. The target compounds have been synthesized via interaction of either 4-amino-6-(tert-butyl)-3-hydrazinyl-1,2,4-triazin-5(4H)-one or 6-(tert-butyl)-3-hydrazinyl-1,2,4-triazin-5(2H)-one with a wide range of compounds with a carbonyl group in moderate to high yields. Molecular structures of the synthesized compounds were confirmed by 1H NMR, 13C NMR, and elemental analyses. The antioxidant activity of these compounds against ascorbic acid was screened to determine their potential as promising oxidative stress suppressors. Our data showed that hydrazones derived from 4-amino-6-(tert-butyl)-3-hydrazinyl-1,2,4-triazin-5(4H)-one are the most active antioxidants among all tested compounds. Furthermore, 3 compounds of this series have been proved to be twice as active as ascorbic acid does. The conclusions are substantiated for in-depth investigations of these derivatives as promising agents for the treatment of disorders accompanied by oxidative stress.