By Vallarie Burge and Elizabeth Sullivan
Faculty mentor: Dr. Davis Oldham
Tuberculosis (TB) is a common disease that, over time, can become resistant to the drugs that combat it. The KsA enzyme that synthesizes the bacterial wall of TB is the target of the TB drug in this project. A computer analyzed potential compounds that could produce a successful KsA inhibitor, and this project set out to make one of them. The analogue would be created by first doing a Grignard addition of 1,4-dibromobenzene with 1-Benzyl piperidin-4-one. The Grignard addition resulted in too many by-products, so from then on, a corrected grignard
product that had the deprotected nitrogen on piperidine was used. Then, after deprotecting the nitrogen in the Grignard product with Pd/C, ammonium formate, celite, and methanol, the alcohol on 1-Pyrenemethanol was chlorinated to create the final analogue. The melting point of the product was 151.2-153.05°C, indicating that 1-chloromethylpyrene was made. By alkylation,
the products of the grignard reaction and the chlorination reaction to create the product. Unfortunately, this did not produce a potential TB drug. The grignard reaction and the alkylation reaction did not result in the necessary products in order to produce the drug.
