Trichomoniasis is one of the most common curable sexually transmitted disease that affects 300 million people worldwide and 3.7 million in the United States. Trichomoniasis is caused by the parasitic protozoan Trichomonas vaginalis. The resistance of T. vaginalis to current forms of 5-nitroimidazole treatment: metronidazole and tinidazole, has increased. Meaning that the need for new forms of treatment for trichomoniasis is becoming more prominent. We hypothesize that in order to grow and replicate, the parasite requires the aid of enzyme, uridine nucleoside ribohydrolase (UNH), to scavenge for uracil from its host. Thus, the inhibition of UNH will impede the enzyme from providing the building blocks essential to the parasite’s life cycle. Screening a library of fragments showed 3-(3-methylpyridin-2-yl) benzonitrile demonstrated promising inhibition of UNH. This compound was used as a starting point to create an array of analogs to test their inhibitory effects on the enzyme. Readily available boronic acids were coupled with bromopyridines under palladium catalyzed Suzuki coupling conditions. A major finding was the increase in inhibition when the nitrogen on the pyridine moiety was shifted to the meta position, as well as having a hydroxyl group in place of the nitrile. Future work will include building on this key structure with additional substituents to compare how IC50 values are affected. The synthesis and inhibitory effects (IC50 values in micromolar) of each analog will be discussed.

Synthesis of phenyl pyridines via suzuki cross coupling to test their inhibitory effects on uridine nucleoside ribohydrolase (UNH)

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.