The ability to mimic biological functions is a key advantage in using modified nucleosides for chemotherapy and antibiotics. Brominated modified nucleosides are convenient intermediates for a wide array of nucleoside derivatives including aromatic substitutions. The chemotherapy pharmaceutical Imatinib uses aromatic structures to emulate adenosine triphosphate; by using brominated nucleosides, similar aromatic substructures could be added. We hypothesize that the resulting compound would be functionally similar to Imatinib while also expressing the benefits of being a modified nucleoside. Furthermore, modified nucleosides have previously been shown to have antibacterial functionality. Herein we report the synthesis of brominated and phenolated nucleoside intermediates along with antibacterial application. Brominated compounds were synthesized by the use a modified Appel reaction while phenolated compounds utilized a modified Gabrial-Mitsunobu reaction and Williamson ether reaction. The brominated modified nucleosides were taken forward to antibacterial testing due to their ability to react with a large variety of aromatic substructures. The bacteria chosen for testing included three gram positive and three gram negative bacteria, Staphylococcus aureus, Escherichia coli, Bacillus cereus, Enterococcus faecalis, Proteus vulgaris, and Neisseria meningitides. 5’-bromo adenylyl, 5’-bromo uridyl, and 3’5’-bromo uridyl compounds had percent inhibition of X%, 12%, and 12% respectively against N. meningitides. These results show the promising effectiveness of brominated compounds as antibiotics while simultaneously serving as accessible intermediates for further reactions with aromatics including phenolation.  <br/>

Brominated nucleosides for aromatic substitution: Synthesis and <i>in vitro</i> studies

255th National Meeting (2018)

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Brominated nucleosides for aromatic substitution: Synthesis and in vitro studies