Crystal structure, DFT, antimicrobial, anticancer and molecular docking of (4E)-4-((aryl)methyleneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one

The Schiff bases (4E)-4-((aryl)methyleneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one 3 were synthetized by reaction of aromatic aldehydes 1 and 4-aminoantipyrine 2. Compounds 3 were fully characterized by FTIR, 1H, 13C and DEPT-135 NMR spectroscopies, elemental analyses and also by single crystal X-ray diffraction. Hirshfeld surface analysis was used to quantify the intermolecular interactions in the studied compounds. The H⋯H, O⋯H and C⋯H contacts as well as the some π-π stacking interactions are the most important intermolecular forces in their crystal structures. The calculated vibrational frequencies and GIAO NMR chemical shifts were used to describe the FTIR characteristics and NMR spectra. Compound 3b showed better antimicrobial activity than 3a. Further colorimetric assays for assessing cell metabolic activity were utilized to explore the potential of both compounds as anticancer drugs. Our results showed a potential of 3b as an anticancer drug on HeLa cells at high concentrations which is explained by the molecular docking calculation using MOE program.