Synthesis and Biological Activity Evaluation of Two Derivatives of 7-Aminocephalosporanic Acid

7-Aminocephalosporanic acid (7-ACA) is a component of antibiotics with a cephalosporin skeleton. Its derivatives have a variety of potential bioactivities, including enzyme inhibition activities. This study aimed to optimize 7-ACA derivatives that were yielded by the reaction of 7-ACA with benzoyl and cinnamoyl chloride. Subsequently, the synthetic compounds were evaluated for their antibacterial activities against five pathogenic bacteria, and enzyme inhibition activities using three enzymes, i.e., caspase-3, caspase-7, and tyrosine kinase. Optimization of the amino acylation at C7 of 7-ACA using benzoyl chlorides and cinnamoyl chlorides has yielded compounds 1 and 2. The synthesis was carried out at room temperature and also modified the solvent and reagents from those carried out previously. The structures of the derivatives were determined based on spectroscopic data. The antibacterial test was performed using the paper disk diffusion method as preliminary screening. It demonstrated that both compounds in 2000 µg/mL indicated inhibition against Bacillus subtilis, Pseudomonas aureginosa, Streptococcus epidermidis, and Salmonella typhi. However, the Minimum Inhibitory Concentration (MIC) and the Minimum Bactericidal Concentration (MBC) values of both compounds showed weak activity. Nevertheless, compound 2 indicated better antibacterial activity against B. subtilis than compound 1. In addition, compounds 1 and 2 showed weak to moderate inhibition against caspase-3, caspase-7, and tyrosine kinase enzymes. This study is the first report of the inhibitory activity of 7-ACA derivatives against the pathogenic bacteria and those three enzymes.