A novel pyridine-based Schiff base with multi-target pharmacological potential: Synthesis, biological evaluation, and molecular docking analysis

In the present study, a novel Schiff base derived from pyridine-4-carboxaldehyde and 4-aminobutan-1-ol was synthesized via a condensation reaction and purified by recrystallization from a DMF/water solvent system. The compound was characterized by IR, 1H-NMR, and 13C-NMR studies. The pharmacological potential of a synthesized compound was evaluated through cell viability and enzyme inhibition assays. The compound exhibited selective cytotoxicity toward MCF-7 breast cancer cells compared to non-tumorigenic MCF-10A cells, with IC₅₀ values of 6.5 mM and 21.8 mM, respectively. In enzyme inhibition studies, the compound showed dose-dependent inhibitory activity against HIV-1 reverse transcriptase, acetylcholinesterase, and α-glucosidase, with IC₅₀ values ranging from 11 to 14 mM. Notably, HIV-1 RT displayed higher sensitivity at lower concentrations. These findings suggest that the compound has multi-target pharmacological potential and may serve as a promising lead for further investigation. Molecular docking was employed to evaluate the binding behavior of a newly synthesized Compound I against HIV-1 reverse transcriptase, epidermal growth factor receptor, and acetylcholinesterase. Docking results revealed that Compound I exhibited moderate binding affinity toward all three targets, with a relative preference for acetylcholinesterase, as evidenced by favorable binding energies and key intermolecular interactions. Although its predicted affinities were lower than those of established reference inhibitors, Compound I demonstrated stable binding orientations and conserved interaction patterns within the active sites. These findings suggest that Compound I may serve as a promising lead scaffold for further structure-based optimization.