10. Esterification of Tetralol and Benzoic Acid Analogs

Austin Fisher University of Saint Francis
Faculty Sponsor(s): Dennis Roberts University of Saint Francis
A series of esters were synthesized by reacting α-tetralol with different analogs of benzoic acid. The compound α-tetralol shares the basic structure of 1,4-naphthaquinone and its derivatives, which have displayed anti-cancer activity through down-regulation of glucose transport. A consistent target to down-regulate is through GLUT1 inhibition, for which these synthesized esters are intended. Esterification of α-tetralol with the different carboxylic acids was performed using catalytic 4-dimethylaminopyridine (DMAP) and coupling agent 1-ethyl-3-(3-dimethylaminopropyl)carboiimide (EDC) as well as one synthesis utilizing diisopropylethylamine (DIEA) instead; however, the latter acid chloride method generated a less stable product. Reaction completion was gauged through TLC and initial conformation of compounds through IR spectra. The Structure-Activity Relationship (SAR) approach is currently in progress, through cell viability assays. Upon completion of the assays, the results will further guide this synthesis.
Chemistry
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Irwin Library 1st Floor