Novel 6-aryl-7-alkyl/aryl-[1,2,4]triazolo[4,3-a][1,3,5]triazine-5(6H)-thiones, processes for their preparation, characterization and evaluation of their in vitro antioxidant activity

Abstract

ABSTRACT. A series of nine new 6-aryl-7-alkyl/aryl-[1,2,4]triazolo[4,3-a][1,3,5]triazine-5(6H)-thiones (2a-i) were synthesized by a reaction of N-triazol-3-yl imidates (1) with three different isothiocyanate derivatives (RNCS)  in refluxing toluene. The structures of the final heterocyclic compounds were confirmed by ¹H-NMR, ¹³C-NMR, FT-IR, elemental analysis, and mass spectral analysis. The target compounds (2a-i) were in vitro screened for their activity as antioxidants using DPPH (2,2′-diphenyl-1-picrylhydrazyl) and FRAP (ferric reducing/antioxidant power) methods. The results revealed that some triazolotriazine-5-(6H)thiones exhibited antioxidant activity ranging from moderate to high. The obtained findings revealed that the triazolotriazine-5-(6H)thiones (2g, 2h, and 2i) have superiority among all compounds, It is obvious that the presence of a hydroxyl group in the structure is essential for the antioxidant properties and should be taken into consideration in further design of structures with potential antioxidant properties.

KEY WORDS: Imidates, Isothiocyanates, Antioxidant, Triazole, DPPH, FRAP

Bull. Chem. Soc. Ethiop. 2021, 35(3), 565-572.

DOI: https://dx.doi.org/10.4314/bcse.v35i3.8