Synthesis, characterization, docking, and antioxidant studies of novel pyrazole molecules

Abstract

In the current study, new Schiff base compounds 1–4 were synthesized by the combination of various aldehydes such as propionaldehyde, cinnamaldehyde, furan-2-carbaldehyde and thiophen-2-carbaldehyde with pyrazole-functionalized amines using a magnetic stirrer. Characterization (color, appearance, melting point, IR, mass, 1H and 13CNMR, and single-crystal XRD analysis), antioxidant characteristics, and molecular docking investigations of the synthesized compounds were explored in this work. The crystal data of the heteroatom isomers (i.e., compounds 3 and 4) are discussed in detail, where the pyran and thiopyran are in the planar conformation and molecule 3 is stabilized with a range of hydrogen bonds, although both 3 and 4 are stabilized with inter- and intra H-bonds, and π…π interactions. The antioxidant properties of compounds 1–4 were assessed using an in vitro DPPH assay. In comparison to the ascorbic acid standard (98.95 %), compound 1 (96.10 %) expressed parallel antioxidant potential at a concentration of 0.4 mg/mL. Molecular docking simulations were performed to identify the binding interactions between these compounds and target biomolecules. Compound 2 ensured the greatest binding (Glide score −7.98) to the epidermal growth factor receptor (EGFR) protein.