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

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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 synthesized compounds was screened by a DPPH radical scavenging assay, reducing power assay, and ferric reducing antioxidant power assay. Among the synthesized 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.

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Authors and Affiliations

  1. Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, 50254, Kaunas, Lithuania

    Ingrida Tumosienė & Ilona Jonuškienė

  2. Laboratory of Physical Organic Chemistry, Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, 1006, Latvia

    Sergey Belyakov

  3. Department of Physical and Inorganic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, 50254, Kaunas, Lithuania

    Kristina Kantminienė

Authors
  1. Ingrida Tumosienė
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  2. Ilona Jonuškienė
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  3. Sergey Belyakov
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  4. Kristina Kantminienė
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Correspondence to Kristina Kantminienė.

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Tumosienė, I., Jonuškienė, I., Belyakov, S. et al. The synthesis of disubstituted 4-methyl-N,N-dipropylbenzenamine derivatives bearing identical azolethione(thiol) moieties as antioxidant agents. Monatsh Chem 154, 1161–1176 (2023). https://doi.org/10.1007/s00706-023-03119-7

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  • DOI: https://doi.org/10.1007/s00706-023-03119-7

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