A Combined Experimental and Computational Approach to a Novel Hydrazone Derivative: Synthesis, Characterization, and In Silico Evaluation
Abstract
A novel sulfonamide based hydrazone derivative, namely (E)-2-(2-(4-(dimethylamino)benzylidene)hydrazinyl)-N-(4-sulfamoylphenyl)acetamide (compound 3), was successfully synthesized from sulfanilamide through a practical three-step method. The structure of the synthesized compound was confirmed by FTIR, 1H NMR, and 13C NMR analyses. The structural, electronic, and biological properties of (E)-2-(2-(4-(dimethylamino)benzylidene)hydrazinyl)-N-(4-sulfamoylphenyl)acetamide were investigated using DFT and molecular docking methods. Geometry optimization at the B3LYP/6-311++G(d,p) level confirmed the stability and polar nature of the molecule. Frontier orbital analysis revealed a HOMO–LUMO energy gap of 4.209 eV, indicating high stability, while MEP analysis identified key reactive regions localized on oxygen and nitrogen atoms. Docking studies against the Adenosine A2A receptor (PDB ID: 2YDO) showed a strong binding affinity of -8.3 kcal/mol, supported by favorable non-covalent interactions. These findings suggest that the molecule is a promising candidate for further drug development, warranting additional experimental validation.
Keywords
Hydrazone, Sulfanilamide, Organic Synthesis, Theoretical Modeling, Molecular Docking
Supporting Institution
Yozgat Bozok University Science and Technology Practice & Research Centre
Project Number
FLO-2025-1745
Thanks
Yozgat Bozok University Science and Technology Practice & Research Centre
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