SYNTHESIS AND EVALUATION ANTIOXIDANT ACTIVITY OF 3-ARYL-5,6,7,8-TETRAHYDROTHIAZOLO[3,2-a][1,3]DIAZEPINES
DOI:
https://doi.org/10.32782/pcsd-2024-4-4Keywords:
thiazolo[3,2-a][1,3]diazepines, 1,3-diazepane-2-thione, α-bromoacetophenones, cyclocondensation, antioxidant activityAbstract
The 1,3-diazepine core is part of many biologically active compounds, for instance, the natural product coformycin with antiviral and anticancer effects, the anticancer drug pentostatin, and the β-lactamase inhibitor avibactam. Our analysis of literature sources showed that thiazolo[3,2-a][1,3]diazepines, which have proven potential anticonvulsant agents and inhibitors of platelet aggregation, have received increased attention from scientists in recent decades. The short-acting hypnotic HIE-124 is worth noting among them which has the potential to be used with sodium thiopental to maintain anesthesia for a longer period. The subject of the presented research is the synthesis and assessment of antioxidant activity of 3-aryl-5,6,7,8- tetrahydrothiazolo[3,2-a][1,3]diazepines. 1,3-Diazepane-2-thione was used as a basic substrate in a cyclocondensation reaction with α-bromoacetophenones to obtain the target 3-aryl-5,6,7,8-tetrahydrothiazolo[3,2-a][1,3]diazepines. The composition and structure of the synthesized derivatives was reliably proven by a set of physical and chemical analyses, including 1H-, 13C-NMR spectroscopy and chromatography-mass spectrometry, as well as elemental analysis data. The antioxidant activity of the synthesized 3-aryl-5,6,7,8-tetrahydrothiazolo[3,2-a][1,3]diazepines was assessed by the inhibition of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. The screening results showed that all derivatives are characterized by promising antioxidant activity with radical absorption level of 90.6 – 97.6 %. The highest rate of inhibition was demonstrated by 3-(4-bromophenyl)-5,6,7,8-tetrahydrothiazolo[3,2-a][1,3]diazepine 6 (I = 97.6 %), and the lowest by 3-(3-nitrophenyl)-5,6,7,8-tetrahydrothiazolo[3,2-a][1,3]diazepine 4 (I = 90.6 %).
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