Zwitterionic pyrimidinium adducts as antioxidants with therapeutic potential as nitric oxide scavenger

• Twenty two compounds incorporating the pyrimidine moiety were prepared.
• The structure of 4c, e, i were confirmed by single-crystal X-ray diffraction.
• Zwitterionic adducts were evaluated for their nitric oxide scavenging potential.
• Compound 4c (IC50 = 69 ± 1.66 μM) exhibited the highest cytotoxicity on nitric oxide.

A variety of zwitterionic adducts were synthesized by using means green chemistry method. The products contain the biologically active barbituric acid moiety embedded in zwitterion products. Both features are pharmaceutically relevant. The chemical structures were deduced by 1H-, 13C-, NMR and HRMS spectral analysis, and X-ray diffraction techniques. In vitro evaluation for the antioxidant activities were carried out towards the inhibition of nitric oxide (NO) radical, known to regulate a mechanism of signals for various cellular functions. NO also play an important role as a mediator of various pathological conditions responsible for cellular damages such as strokes, cancers, diabetes, chronic heart failure and inflammatory disease and various neurodegenerative disorders. All tested compounds were found to be more potent nitric oxide scavengers as compared to standard drug ascorbic acid (IC50 = 618 ± 2.0 μM). Compounds 4c and e exhibiting several hundred fold more activity against nitric oxide radical with IC50 values of 69 ± 1.66 and 70.1 ± 0.89 μM respectively, as compared to standard drug ascorbic acid (IC50 = 618 ± 2.0 μM).

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