Some studies performed in our laboratory on pyrrole and its derivatives pointed towards the enrichment of the evaluations of these promising chemical structures for the potential treatment of neurodegenerative conditions in general and Parkinson's disease in particular. A classical Paal-Knorr cyclization approach is applied to synthesize the basic hydrazine used for the formation of the designed series of hydrazones (-). The potential neurotoxic and neuroprotective effects of the newly synthesized derivatives were investigated in vitro using different models of induced oxidative stress at three subcellular levels (rat brain synaptosomes, mitochondria, and microsomes). The results identified as the least neurotoxic molecules, , , and applied at a concentration of 100 µM to the isolated fractions. In addition, the highest statistically significant neuroprotection was observed for and at a concentration of 100 µM using three different injury models on subcellular fractions, including 6-hydroxydopamine in rat brain synaptosomes, tert-butyl hydroperoxide in brain mitochondria, and non-enzyme-induced lipid peroxidation in brain microsomes. The MAOA/MAOB inhibitory activity of the new compounds was studied at a concentration of 1 µM. The lack of a statistically significant MAOA inhibitory effect was observed for all tested compounds, except for , which showed 40% inhibitory activity. The most prominent statistically significant MAOB inhibitory effect was determined for , , and , comparable to that of selegiline. The corresponding selectivity index defined as a non-selective MAO inhibitor and all other new hydrazones as selective MAOB inhibitors, with indicating the highest selectivity index of >471. The most active and least toxic representative () was evaluated in vivo on Rotenone based model of Parkinson's disease. The results revealed no microscopically visible alterations in the ganglion and glial cells in the animals treated with rotenone in combination with .