Molecules with a benzofulvene motif were synthesized in high yield via a pseudo-condensation of phenyl indenyl lithium with substituted aryl aldehydes. In the optimization of this synthetic method, our group varied several factors including: reaction temperature, solvent, and metal stabilizing group. We then utilized quantitative NMR to determine yields via an internal standard. At present our optimized procedure has yields above 80%. We have now turned our attention towards medicinal applications of the benzofulvene motif. Utilizing protein modeling docking software, we have investigated the utility of the benzofulvene motif as a Flavoprotein active site inhibitor. We have modeled benzofulvene motifs, having determined binding affinities of up to -9.6 kcal/mole to the active site of Human Thioredoxin Reductase, an enzyme targeted in possible anti-carcinogenic pharmaceuticals. Our facile synthetic route may provide a new means of combating aggressive cancer types.

Highly functionalized aromatics: An investigation into the synthesis and flavoprotein inhibiting properties of benzofulvene motifs

245th National Meeting (2013)

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