Combined experimental and computational approach toward biological, physicochemical and quantum chemical aspects of substituted 1-[5-phenyl-3-(2-trifluoromethyl-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone

In current work, three N-acetyl pyrazoline derivatives (1–3) have been prepared via 1,4-addition reaction of hydrazine on chalcones, followed by cyclization of the adduct in the presence of acetic acid. The structural interpretation of synthesized compounds was accomplished using various characterization techniques like FT-IR, Ultraviolet/visible spectroscopy, 1H NMR and 13C NMR. The synthesized compounds were evaluated for antioxidant, Urease inhibitory and Lipoxygenase inhibitory activities and results revealed that compound 2 showed promising antioxidant, Urease inhibitory and Lipoxygenase inhibitory activity with IC50 values 33.2 ± 0.45, 32.7 ± 0.11 and 42.2 ± 0.77, respectively. Moreover, DNA binding interactions of the N-acetyl pyrazoline derivatives have also been carried out with SS-DNA (Salmon Sperm DNA) using absorption spectroscopy. Furthermore, molecular docking was conducted for a ready comparison with the experimental data and to determine the interactions involved. ADMET profiling of pyrazoline derivatives was also done using Admet SAR. Besides that, quantum chemical calculations using DFT (density functional theory) were carried out to explore optimized geometries, FMOs (Frontier molecular orbitals), NBOs (Nonbonding orbitals) of synthesized compounds and to predict their NLO (Nonlinear optical) properties. The synthesized compounds showed much better NLO behavior than standard Urea along with a strong agreement between computed and empirically recorded spectral data.