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New functionalized N-heterocyclic derivatives were synthesized from an itaconic anhydride (ITA) precursor and characterized by spectral and analytical data. All of the synthesized products were screened for in vitro antioxidant and antimicrobial properties. Among the tested compounds, derivatives 5a and 8a exhibited noticeable DPPH radical scavenging activity, reducing power capacity and nitric oxide scavenging activity compared to standard glutathione. Compound 3d showed strong antibacterial activity, whereas compounds 3a and 4a exhibited potential antifungal activity. Compounds exhibiting good antioxidant activity were docked with tyrosinase enzyme (PDB ID: 3NM8) from Bacillus megaterium to predict their putative interactions.