The synthesis of disubstituted 4-methyl-N,N-dipropylbenzenamine derivatives bearing identical azolethione(thiol) moieties as antioxidant agents

Abstract

Abstract A series of novel 3,3'-(p-tolylazanediyl)di(propanehydrazide) derivatives bearing double sets of thiosemicarbazide, oxadiazolethione, variously N- and S-substituted triazolethione, pyrrole, and hydrazone moieties were synthesized and their molecular structures were confirmed by IR, 1H, 13C NMR spectroscopy and mass spectrometry data. X-ray analysis of 2,2'-((((p-tolylazanediyl)bis(ethane-2,1-diyl))bis(4-phenyl-4H-1,2,4-triazole-5,3-diyl))bis(sulfanediyl))bis(1-(p-tolyl)ethan-1-one) crystal has revealed, that the molecules in the crystal are associated by means of intermolecular hydrogen bonds of OH···N type, forming centrosymmetric dimers. The antioxidant activity of the synthesised compounds was screened by a DPPH radical scavenging assay, reducing power assay, and ferric reducing antioxidant power assay. Among the synthesised compounds, 2,2'-(3,3'-(p-tolylazanediyl)bis(propanoyl))bis(N-phenylhydrazine-1-carbothioamide) has been identified as possessing the highest antioxidant activity, which is 1.25-2 times higher than that of the commercial antioxidant butylated hydroxytoluene.