Schiff bases containing beta-lactam rings: synthesis, characterization, and biological activity

Abstract

The aim of this study is to synthesize biologically active Schiff bases and evaluate their antimicrobial activity of synthesized compound. Schiff bases are synthesized by the condensation reaction of primary amines with aldehydes or ketones. In this research, the synthesis process involves a room-temperature condensation reaction between o-vanillin and ampicillin, a beta-lactam containing antibiotic commonly used to treat bacterial infections. As a solvent for the procedure of the Schiff base synthesis used methanol under mild conditions. Following the synthesis, the structural characterization of the obtained Schiff base is conducted using a combination of spectroscopic techniques, including proton nuclear magnetic resonance (1H NMR) and carbon-13 nuclear magnetic resonance (13C NMR) spectroscopy, as well as high resolution mass spectrometry (HRMS). These analytical methods assist in confirming the successful formation of the target compound and provide insights into its molecular structure and purity. Subsequently, the antimicrobial activity of the synthesized Schiff base is assessed through in vitro antibacterial assays against Staphyloccocus aureus ATCC6538, Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922 and clinical isolate Escherichia coli BDU32. The antibacterial efficacy of the Schiff base is compared to that of the parent antibiotic, ampicillin, to ascertain whether the modification augments, diminishes, or maintains its antimicrobial potential. This comparative analysis furnishes valuable information on the structure-activity relationship and the potential of Schiff bases as novel antibacterial agents. The outcomes of this study contribute to the ongoing research in medicinal chemistry, particularly in the development of Schiff base derivatives as potential drug candidates with enhanced pharmacological properties.