Synthesis, structural identifications of bioactive two novel Schiff bases

Abstract

Two new Schiff base compounds with high biological activity were derived from the condensation reaction of two substitute aldehydes (10-chloroanthracene-9-carbaldehyde/8-hydroxyquinoline-2-carbaldehyde) and 4-aminoantipyrine. The first Schiff base is 4-(((10-chloroanthracene-9-yl)methylene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazole-3-one and the second Schiff base is 4-(((8-hydroquinoline-2-yl)methylene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazole-3-one. In this report the various spectroscopic analysis (FT-IR, NMR, LC-MS/MS and single-crystal X-ray Single Crystal diffraction technique) and Hirshfeld surface analysis and fingerprint plots (a detailed analysis of the intermolecular interactions and crystal packings) of these compounds are presented. Both the density functional theory (DFT/B3LYP/6-31G (d)) and Hartree Fock (HF/6-31 + G (d)) calculations are used for computational modeling. The vibration frequencies are calculated by using these two methods. Theoretical data were then compared to the experimental data from IR spectra. Furthermore, biological potential of the compounds were evaluated through bioassays such as antimicrobial and antioxidant properties and cytotoxic activities in MCF-7 human breast cancer cell line (p < 0.05). When the capacity for biological activity has tested the compound containing 8-hydroxyquinoline ring was found to have higher biological activity than the compound containing 10-chloroanthracene. An excellent agreement was found between our theoretical calculations and the experimental data. Our findings suggest that both chemicals might have potential as medicinal properties. (C) 2019 Elsevier B.V. All rights reserved.