A Synthetic, Spectroscopic, Theoretical and Biological Perspective on a Novel Schiff Base Included 4-Aminoantipyrine

Abstract

A novel Schiff base, 4-(([1,1'-biphenyl]-4-ylmethylene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one (BiPhAAP), obtained from biphenyl carboxaldehyde with 4-aminoantipyrine was characterized using elemental analysis, FT-IR, and 1H and 13C NMR spectroscopic methods. In addition to the spectroscopic findings, geometrical descriptions and the extent of surface interactions in the compound were determined by X-ray single crystallographic and Molecular Hirshfeld surface (MHS) analysis techniques. The distinctions between experimental and calculated FT-IR results have proved the presence of intra-molecular (C–H….O type) hydrogen bonds in the crystal structure. The in vitro antimicrobial potential, which was studied against two Gram-negative (Escherichia coli and Proteus vulgaris) and two Gram-positive (Bacillus subtilis and Micrococcus luteus) bacterial strains, and three yeast strains (Candida albicans, Aspergillus niger and Candida globrata) was examined by using the agar well diffusion method at concentrations of 250, 125 and 62.5 mg/mL. The in vitro antioxidant activities of this compound were estimated by five different antioxidant assays (DPPH radical scavenging, reducing power, metal chelating activity, superoxide scavenging, and total antioxidant). Cytotoxic activity of the new compound was sought against human breast carcinoma cells (MCF-7). The IC50 values were established with respect to the MTT test.