By Carleigh McDonald and Maria Schneider
Faculty mentor: Dr. Davis Oldham
Tuberculosis (TB) is a serious illness that is caused by the Mycobacterium tuberculosis bacterium attacking the body. The previously most effective drugs in fighting TB are becoming increasingly ineffective as strains of MDR (multidrug-resistant) TB are becoming more common. To combat this setback, development of a possible new drug that attacks the key enzyme in the survival of the bacteria,
b-ketoacyl ACP synthase 1 (Kas A), via an inhibitor was explored. To develop an inhibitor, the lead compound (a piperidinol) underwent a Grignard addition, deprotection of a nitrogen group, chlorination of alcohols, and an SN2 reaction with amine nucleophile. Following the reactions, the lead compound
was varied to attach two new functional groups: a trifluoromethyl and pyrene group. The desired Grignard product was not achieved, proven by a lack of relative peaks in a GC (Gas Chromatography) spectrum. However, the deprotection of nitrogen, chlorination, and SN2 reaction proved successful by
relative IR peaks and C-13 NMR (Nuclear Magnetic Resonance) spectra. Procedurally, the reaction proved successful in most desired reactions. Proving the product’s effectiveness in acting as an inhibitor will require future experimentation.
