Synthesis of novel chromeno-tethered imidazolone scaffold through one pot sequential multicomponent reaction mediated cyclization: A structural, computational and in silico investigation

•Synthesis of novel chromeno imidazole-based derivative.•Spectroscopic characterizations of the synthesized compound.•Structural analysis using single crystal X-ray diffraction technique.•Optimized structure, frontier molecular orbital and molecular electrostatic potential map of the compound were performed using DFT.•Computational molecular dynamics simulation was performed to assess the stability of the ligand protein complex. A novel chromeno imidazole-based derivative was synthesized and characterized using single crystal X-ray diffraction technique. The MCR strategical methodology followed by the cyclization and the SN2 mechanism resulted in the formation of chromenoimidazolone molecular scaffold. The structural analysis revealed that the structure crystallizes in P1¯ space group and was stabilized by intra and intermolecular interactions. The dihedral angle of 82.85° indicated the non planarity of the molecule. The molecular interactions exhibited by the crystal structure were analysed by the Hirshfeld surface analysis and the H…H interactions was found to be major contributor to the overall interactions of the compound with the percentage contribution of 52.3%. The theoretical investigations were carried out using density functional theory calculations to predict various electronic properties of the compound. The HOMO-LUMO energy gap of the compound is found to be 1.4534 eV for alpha and 3.9367 eV for a beta spin. The MEP analysis revealed that the C = O exhibit the highest negative electrostatic potential with the value of -0.064 a.u. indicating its nucleophilic nature. Further, natural bond orbital analysis revealed that the LP(1)→π* interaction demonstrates the highest stabilization energy of 53.49 kcal/mol. The results of the molecular docking analysis of the compound against 6FS1 protein showed a docking score of -7.4 kcal/mol, indicating the potential of the compound to be a good anti-cancer agent. Further, the findings of the molecular docking were substantiated by the molecular dynamics simulation studies which showed very good stability of the protein-ligand complex.