Microwave-Assisted Synthesis And Antibacterial Activity Of Phenylacetic Acid Derivatives On Bacterial Pathogens

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Master of Science

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Infectious diseases are a worldwide concern. The increase in the frequency of antibiotic resistance in pathogenic bacteria combined with the decline in the development of new antibiotics has led to the need for alternate ways of treating infectious diseases. In this study, we are exploring the synthesis and potential antimicrobial properties of plant-derived phenylacetic acids against multiple drug resistant bacterial pathogens. Towards this, several phenylacetic acids synthesis were studied utilizing microwave-assisted base hydrolysis of their corresponding acetonitriles. Through these studies, an efficient, fast, and straightforward microwave-assisted protocol was developed for converting nitriles to acids. The effects of solvents, temperature and time on the yield and purity of the phenylacetic acids was evaluated to provide the optimum conditions required. Nine phenylacetic acids and two aromatic acids have been synthesized in yields ranging from 64 – 99% following this protocol. A protocol was successfully developed to accomplish the synthesis of the amides without proceeding to the corresponding acid. All compounds synthesized have been fully characterized using NMR, IR and GC/MS. Preliminary testing results on the antimicrobial activity of phenylacetic acid (PAA), 4-hydroxyphenylacetic acid (HPAA), and 2-fluorophenylacetic acid (2-FAA) suggest a significant growth inhibition on Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa.