Synthesis, crystal structure, Hirshfeld surface, DFT and docking studies of 4-[(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(phenyl)methyl]-5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one

In the present work, 4-[(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(phenyl)methyl]-5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one (BPZ) was synthesized by one pot multicomponent reaction of ethylacetoacetate, phenylhydrazine and benzaldehyde in the presence of Ce-MCM-48 catalyst. The title compound was characterized by FT-IR, H-1 NMR, and C-13 NMR spectral studies and single crystal XRD technique. The intermolecular contacts of the title compound were studied by Hirshfeld surface (d(norm) surfaces and 2D fingerprint plots) analysis whereas an intra-molecular hydrogen bonding interaction was examined through NCI-RDG plot. The geometry of the molecular structure was optimized by using the density functional theory (DFT) at B3LYP/6-311 g(d,p) level. Molecular electrostatic potential (MEP), natural bond orbital (NBO) analysis, nonlinear optical properties (NLO) and global chemical reactivity parameters (GCRP) were described through computational method. Further, the molecular docking study was done for title compound with COVID-19 caused protein structure (6LU7, nCoV-SARS-2 M-pro). The study revealed that the significant conventional hydrogen bonding and other interactions were observed between the active amino acid residue of SARS-nCoV-2 M-pro and BPZ ligand. (C) 2021 Elsevier B.V. All rights reserved.

Automated summary

In this study, the compound BPZ was synthesized using Ce-MCM-48 catalyst and characterized by various spectroscopic techniques. Molecular structure was optimized using DFT, and the compound's interactions with the COVID-19 protein structure were investigated through molecular docking study, revealing significant hydrogen bonding interactions.