Dual Inhibitory Potential and Comprehensive Investigation of a Bis(semicarbazone) Ligand: A Comparative Study with Its Precursor

This study presents a comparative investigation into the multidentate bis(semicarbazone) ligand, (۲Z,۲’E)-۲,۲’-(((propane-۱,۳-diylbis(oxy))bis(۲,۱-phenylene))bis(methanylylidene))bis(hydrazine-۱-carboxamide) (H₂L), and its precursor L. The synthesis of L involved a two-step process: the formation of potassium ۲-formylphenolate, followed by a reaction with ۱,۳-dibromopropane. H₂L was synthesised through the reaction of L with semicarbazide in a ۱:۲ mole ratio. Comparative analysis between L and H₂L was carried out using various analytical and spectroscopic techniques, including FT-IR, UV-Vis, mass spectrometry, ۱H- and ۱۳C-NMR, elemental analysis and melting points. Further comparative studies explored their thermal properties, Density Functional Theory (DFT) simulations, and molecular docking. DFT simulations using the B۳LYP functional at the ۶-۳۱۱++G(d,p) level provided insights into the stability, electronic properties, and geometries of both compounds. Molecular docking studies against drug discovery targets ۵IQ۹ and ۵VBU revealed comparative binding energies and interaction profiles, indicating potential dual inhibitory effects. Significantly, biological assessments showed that while L exhibited moderate antibacterial activity, H₂L demonstrated improved antifungal efficacy, particularly against Candida albicans, highlighting its potential as a therapeutic alternative.

کلیدواژه ها:

Multidentate ligand ، Characterisation ، thermal properties ، DFT calculations ، Molecular docking ، Dual Inhibitory Potential ، Antimicrobial efficacy