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Chemistry
Completed Project

Progress Towards Synthesis of Some Antimicrobial Marine Natural Products

Anne-Marie Abban-Demitrus ’21 and Professor Nicholas Dodge

The goal of this study was to effectively synthesize 4-Amino-N-(2,6-dioxo-1,2,3,6-tetrahydro-4-pyrimidinyl) benzamide. The compound is a relatively unknown marine natural product which has shown some significant antimicrobial activity against some disease-causing mycobacterium. The compound itself can theoretically be synthesized through the amide coupling of 4-aminobenzoic acid and 4-Amino-2,6-dihydroxypyrimidine – better known as 6-aminouracil. We endeavored to make a model compound using benzoyl chloride (more reactive than the carboxylic acid) in order to understand the reaction properties of 6-aminouracil. However, after extensive experimentation with different reaction conditions, we were unable to make this model compound, owing to the fact that 6-aminouracil is – for the most part – a relatively unreactive molecule, responding only in highly specific reaction conditions. We theorize that 6-aminouracil’s low reactivity is due to the fact that the amine group (the moiety expected to react) on 6-aminouracil is resonance stabilized. Owing to this issue, the focus shifted from the use of 6-aminouracil to 5-aminouracil, its exponentially more reactive constitutional isomer, as the preferred reactant. This shift yielded successful results and we were able to synthesize the natural product isomer, which we will use for biological activity studies. The study was then dedicated to building a compound library of the natural product derivatives – each of which could contain unique antibiotic properties.