Synthesis, characterization, and biological evaluation of a β-amino carbonyl and its metal complexes using guanine hydrochloride catalyst

Abstract

In this study, we synthesized 3-(4-chlorophenyl amino)-1,3-diphenyl propane-1-one and its Cu(II), Zn(II), and Ni(II) metal complexes using the novel catalyst, guanine hydrochloride. The synthesized compounds were characterized using UV–Vis, FT-IR, HRMS, elemental analysis, ¹HNMR, and ¹³CNMR techniques. Subsequently, the antioxidant and antibacterial potential (biological activity) of the compounds were evaluated. Antioxidant activity was assessed using DPPH radical scavenging, H₂O₂ hydroxyl scavenging, and FRAP assay methods, while antibacterial activity was determined via disc-diffusion method against gram-positive (Bacillus subtilis and Staphylococcus aureus) and gram-negative (Erwinia amylovora and Escherichia coli) bacteria. Ligand–protein interactions were examined using molecular docking studies. Guanine hydrochloride, the catalyst used, improved reaction time and operated under room temperature, and was easily removed. The ligand exhibited superior antioxidant potential (IC₅₀ = 470.916 ± 0.30 ppm) compared to its metal complexes in all three assays. Among the tested compounds, the Cu(II) metal complex showed the largest zone of inhibition (4–9.9 mm) against all bacteria. The metal complexes displayed better binding energy than the ligand, proving the compounds’ candidacy for future therapeutic applications.

Graphical abstract

Benzaldehyde, p-chloroanilines and acetophenone were allowed to react in this multi-component reaction to form b-amino carbonyl. Metal salts of Cu(II), Zn(II) and Ni(II) were mixed with the ligand to form metal-ligand complexes. The formed products were tested for their anti-oxidant and antibacterial activity, which showed appreciable results.