Synthesis, Crystal Structure and Computational Investigation of New 4-Phenyl-decahydro-1H-1,5-benzodiazepin-2-one as Potent Inhibitor of Mu-opioid Receptor

A novel benzodiazepine derivative was prepared and characterized by elemental analysis, FT-IR, NMR (1H and 13C) and HR-MS methods. Its crystal structure was also investigated by single crystal X-ray diffraction. In the title compound, the fused 6- and 7-membered rings adopt chair and “twist boat” conformations, respectively. In the crystal, the molecules form inversion dimers through N—H⋅⋅⋅O hydrogen bonds and pack with no unusually short intermolecular contacts, which is in agreement with the results of the Hirshfeld surface analysis. The Hirshfeld surface analysis showed that the H⋅⋅⋅H contact was the most important interaction for the studied compound. Based on the DFT−B3LYP study, the studied compound owned a little different geometry in the gas phase concerning the solid phase. The molecular docking was performed between the title compound and a mu-opioid receptor. Molecular dynamics studies were also carried up to 50 ns to understand the stability for the title compound complex with the mu-opioid receptor.