Quantum-Chemical Investigation, Reactivity, NBO, Docking-Based Exploration and in Silico Pharmacological Properties of 3-Bromo-2-[(2Z)-2-(2-oxonaphthalen-1(2H)-ylidene)hydrazinyl]benzoic Acid

Hydrazone derivatives have gained significant attention in medicinal chemistry as promising candidates to address critical therapeutic challenges, particularly antibiotic resistance. Their unique structural and electronic properties enable diverse biological interactions, positioning them as valuable scaffolds for drug development. In this work, we used computational approaches to evaluate the electronic and biological properties of 3-bromo-2-[(2Z)-2-(2-oxonaphthalen-1(2H)-ylidene) hydrazinyl] benzoic (BrOHBA). Quantum chemistry computations using the B3LYP/6-311++G(d,p) level of calculation elucidate details about the molecule’s reactivity, stability, and favorite sites for nucleophilic and electrophilic attacks. Natural bond orbitals (NBO) analysis revealed delocalization effects around the phenyl ring, which were connected to significant bioactivity. The nature of interactions within a molecule can be determined using reduced density gradient (RDG) analysis and interaction region indicator (IRI) topology analysis. Molecular docking simulations using AutoDock Vina demonstrated strong binding affinity against prolyl aminopeptidase (PAP) (PDB: 1QTR). The compound’s favourable ADMET profile further supports its drug development potential. These comprehensive computational insights position BrOHBA as a lead candidate, warranting experimental validation for infectious disease applications.