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In this study, we examined the potential anti-Alzheimer’s and antioxidant activities of 12 analogs of coumarin and flavone compounds. Notably, nitro coumarins 6 and 7 demonstrated noteworthy activity against acetylcholinesterase, although they did not exhibit antioxidant properties. Among the tested compounds, four flavones and one coumarin displayed dual activity as both inhibitors of acetylcholinesterase and antioxidants. Particularly, flavone 9 exhibited exceptional antioxidant activity as well as substantial anti-cholinesterase activity. Molecular docking techniques were employed to investigate the relationship between the anti-Alzheimer’s and antioxidant potential of the compounds. Intriguingly, compound 9 displayed the strongest binding energy values with both monoamine oxidase-B (MAO-B) enzyme (−15.70 kcal/mol) and acetylcholinesterase enzyme (−21.70 kcal/mol), indicating that its antioxidant activity may be attributed to MAO-B inhibition. The pharmacokinetic and safety profiles of five compounds (5, 6, 7, 8, and 9) were examined using pkCSM server, revealing varying characteristics in absorption, CYP enzyme interactions, and toxicity. Compound 8 displays high absorption and lower toxicity, while Compound 6 emerges as a promising candidate due to favorable overall attributes. Nonetheless, comprehensive evaluation, including clinical studies, is crucial for determining their suitability for human use.

In silico and in vitro profiling of coumarins and flavonoids for anti-Alzheimer and antioxidant activity