(2E)-2-[1-(1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-N-(4-methoxyphenyl)hydrazinecarboxamide: Synthesis, crystal structure, vibrational analysis, DFT computations, molecular docking and antifungal activity

Abstract

Fungal infections are a growing health threat to mankind. The development of novel potent antifungal agents is a challenge to overcome the resistance to the available antifungal medications. The current report focuses on the synthesis and spectroscopic characterization of a new imidazole-bearing antifungal agent. The vibrational characteristics of the title compound are explored using Fourier transform infrared and Raman spectroscopy with the aid of density functional theory. Highest occupied and lowest unoccupied molecular orbital investigations and natural bond orbital analysis of the title molecule are performed to investigate the possible intermolecular delocalisation or hyper-conjugation, and the possible interactions with the target protein. Single crystal X-ray analysis confirms the assigned (E)-configuration of the imine double bond structure of the title compound. The molecular structure of the title compound is crystallised in a monoclinic space group, namely, P21/c, a = 10.7007 (4) Å, b = 7.3072 (3) Å, c = 24.9088 (8) Å, β = 97.178 (2)°, V = 1932.41 (12) Å3 and Z = 4. The antifungal potential of the title compound is in vitro assessed against four fungal strains. In addition, molecular docking of the title molecule predicts its binding orientation in the active site of the target protein.