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Edward McIntee, Chemistry


The goal of this investigation was to synthesize novel aromatic azo inhibitors based on an aromatic azo inhibitor discovered from in silico screening against Low Molecular Weight Protein Tyrosine Phosphatase (LMW-PTP). These inhibitors were then tested in vitro aginst LMW-PTP Isoform B. The synthesis of the inhibitor of interest was achieved via a Sandmeyer reaction, utilizing p-aminobenzoic acid. The nucleophile used in the synthesis, 3-hydroxy-2-naphthoic acid, was linked with p-aminobenzoic acid, and the final product was purified via recrystallization. Characterization techniques included 1H-NMR, 13C-NMR, COSY, and HMQC. This newly synthesized product was an analogue to a previously synthesized competitive inhibitor, 156563, which had an inhibitor dissociation constant of 33.5μM. By synthesizing an analogue to inhibitor 156563, our group hopes to probe the carboxylic acid chain length as a function of inhibition.