Synthesis, crystal structure, spectroscopic, quantum chemical investigation, molecular docking and ADMET prediction of 2(E)-3-(anthracen-9-yl)-1-(1-methyl-1H-pyrrol-2-yl) prop-2-en-1-one

Abstract

In the present study, 2(E)-3-(anthracen-9-yl)-1-(1-methyl-1H-pyrrol-2-yl) prop-2-en-1-one (3AMP) crystal was grown by slow evaporation method. The single crystal X-ray diffraction analysis and density functional theory (DFT) calculations were carried out for 3AMP crystal. The 3AMP crystallizes in orthorhombic space group Pbca with a = 14.818 (8) Å, b = 9.796 (5) Å, c = 23.239 (11) Å. Hirshfeld surface and finger print plots were analyzed to confirm the existence of intra-, inter-molecular and other weak interactions using Crystal Explorer. The optimized molecular structure and harmonic wavenumbers were calculated by DFT method using B3LYP functional with 6-31G(d,p) basis set. The FT-IR, 1H, 13C NMR and UV–Vis spectra of 3AMP were recorded and analyzed. The optimized geometrical parameters, calculated wavenumbers by DFT method were compared with the experimental results. Natural bond orbital (NBO) analysis was carried out to evaluate the intra- and inter-molecular interactions in the crystal. The energy gap for 3AMP was calculated as 3.156 eV. Molecular electrostatic potential (MEP), Mulliken atomic charges and non-linear optical (NLO) properties for the title crystal were calculated. In addition, gauge invariant atomic orbital (GIAO) method was used to calculate the 1H and 13C NMR chemical shifts in the ground state. To obtain the electronic transitions in UV–Vis spectra of the title molecule in DMSO and ethanol solvents, TD-DFT calculations were performed on the optimized geometry. Furthermore, the compound was subjected to in silico ADMET evaluation. Molecular docking study was carried out to determine the interactions of ligand with the protein Hyaluronidase (PDB ID: 1FCQ).