Density functional studies and spectroscopic analysis (FT-IR, FT-Raman, UV–visible, and NMR) with molecular docking approach on an anticancer and antifungal drug 4‑hydroxy-3-methoxybenzaldehyde

Abstract

4‑hydroxy-3-methoxybenzaldehyde was investigated quantum chemically by DFT approach, surface analysis by Hirshfeld and experimentally by NMR (FT-IR, UV-Visible 1HNMR and 13CNMR). The B3LYP method and the 6–311 ++ G (d, p) basis set were applied to optimize the molecular structure and to calculate the wavenumbers of normal vibrational modes. A detailed description of the intermolecular interactions of the crystal surface was carried out by means of Hirshfeld surface analysis and fingerprint plots found. The calculated bond lengths and angles were compared with the experimental bond lengths and bond angle parameters and found to be in good agreement. VEDA successfully carried out for the distribution of potential energy. 1HNMR and 13CNMR shifts were estimated using the GIAO method and the results compared with experimental spectra. The molecule reactivity region MEP, molecular stability, NBO, and HOMO-LUMO taken into account. Highest occupied and lowest unoccupied energies were computed and found to be -6.413 eV and -1.873 eV, respectively, indicating charge transfer inside the molecule. Chemical descriptors indicate the reactivity of the molecule as a whole, and Fukui function calculations were used to examine the reactive locations of the compound. NBO analysis indicates that the greatest second order perturbation energy E(2) = 31.26 kcal/mol associated with electron delocalization from the donor LP(2) of O2 → π*(C1-C3) acceptor interaction. Many of the proteins for ligand have been used to examine the biological activity, and the results show that the titled compound may have anti-cancer, antioxidant, and antibacterial activities. The drug-likeness was also studied and molecular docking was done using different proteins and with binding energy -5.9. This system has also been subjected to docking and molecular dynamic simulations in order to better visualize binding sites and the effect of ligand on 7POM conformation. The binding free energy of the receptor protein complex was computed to revalidate the inhibitor affinity for the receptor protein complex predicted by docking and molecular dynamic simulation studies. Binding free energy of docked complex estimated by using MM/PBSA approach.