With the increasing prevalence of neurodegenerative diseases (NDDs) and the limited effectiveness of existing treatments, there is a pressing need to discover new therapeutic leads that can interact with multiple targets implicated in NDD pathogenesis. A novel series of 1,3,4-oxadiazol-2-amine and 1,3,4-thiadiazol-2-amine derivatives has been designed to evaluate the inhibitory potential of these compounds against acetylcholinesterase, tyrosinase, and peroxiredoxins was tested using in silico and in vitro methods. Oxadiazole (4a, 4d) and thiadiazole (4e, 4g, 4h) derivatives were synthesised by cyclisation of schiff base using FeCl3, further characterised by FTIR, 1H NMR and mass spectra. In vitro inhibitory studies evaluated acetylcholinesterase, tyrosinase and peroxiredoxins enzymes. Molecular docking revealed that compounds 4a and 4e effectively interacted against acetylcholinesterase and tyrosinase. In vitro results showed that compounds 4a and 4e exhibited the highest inhibitory activity against acetylcholinesterase and tyrosinase and were good antioxidant agents. The docking results correlated with in vitro results confirmed that compound 4a from the oxadiazole series and compound 4e from the thiadiazole series had the most potent acetylcholinesterase and tyrosinase inhibitory activity. Further analysis suggested that heterocyclic groups might be a reason for better acetylcholinesterase and tyrosinase inhibitory action. This indicates additional scope for these derivatives to be explored further as a neuroprotective agent for a better understanding of the underlying mechanisms and pathophysiology.