EVALUATION OF ANTIOXIDANT ACTIVITY OF 2-(S-METHYLKETOARYL)BENZIMIDAZOLES AND 3-ARYLBENZ[4,5]IMIDAZO[2,1-b]THIAZOLES
DOI:
https://doi.org/10.32782/pcsd-2024-4-5Keywords:
2-{(1H-benz[d]imidazol-2-yl)thio}-1-arylethanones, 3-arylbenz[4,5]imidazo[2,1-b]thiazoles, DPPH analysis, antioxidant activity, structure-activity dependence analysisAbstract
The benzimidazole derivative is one of the most promising types of condensed heterocyclic compounds that are widely used in modern medical and pharmaceutical chemistry. Structural modification of the benzimidazole framework with biooriented fragments made this heterocycle versatile, with a wide spectrum of pharmacological activity. Among such derivatives, numerous benzimidazo[2,1-b]thiazole compounds, which are both drugs and drug candidates, should be noted. Recently, promising agents with antibacterial, antifungal, anti-inflammatory, anti-ulcer, antiviral, anthelmintic and anti-cancer effects have been discovered among them. The high antioxidant activity of 2H-benz[4,5]imidazo[2,1-b] [1,3]thiazin-4(3H)-one against the stable DPPH radical is known, with the inhibition level of 73 %. Thus, studying the antioxidant activity of its new representatives remains a priority task. The work is devoted to the study of the antiradical properties of 3-arylbenz[4,5]imidazo[2,1-b][1,3]thiazoles 4a-h obtained by polyphosphoric acid-initiated cyclization of 2-((1H-benzo[d]imidazole-2-yl)thio)-1-(phenyl-substituted)ethanones 3a-h. Antioxidant activity was assessed using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical inhibition method. The results of the experiment showed that at a concentration of 5 mM 2-{(1H-benz[d]imidazol-2-yl)thio}-1- arylethanones 3a-h demonstrate significantly higher antioxidant activity compared to their cyclic analogues — 3-arylbenz[ 4,5]imidazo[2,1-b]thiazoles 4. Inhibition of DPPH radicals by compounds 3a-h ranges from 80.0 % to 95.6 %, while for compounds 4a-h this varies from 46.7 % to 90.2 %. The highest antioxidant activity was shown by 2-{(1H-benz[d]imidazol- 2-yl)thio}-1-(4-hydroxyphenyl)ethanone 3d (I = 95.6 %), which is fully consistent with literature data for compounds that contain a phenol fragment.
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