Synthesis of 2-Alkyl-Quinolines for Anti-Cancer Testing
Authors:Jennifer An, Edward Laguna
Mentor:Catharine Larsen, Assistant Professor of Chemistry, University of California, Riverside
Quinolines are nitrogen-containing aromatic compounds found in an array of drug therapies, dyes, pesticides, organic light-emitting diodes (LEDs), and ligands for catalysis. Initially synthesized as analogs of alkyl-substituted phenanthrolines, 2-alkyl quinoline compounds lack an entire pyridine ring but surprisingly retain micromolar anti-cancer activity in vitro. The Larsen Lab has developed a solvent-free reaction with water as the by-product to give alkyl-substituted quinolines in a single step, expanding the structures that are rapidly accessible. This increases the probability of finding a quinoline with the ability to suppress tumor growth by killing cancer cells more selectively than healthy cells for reduced side effects. A copper catalyst applied to a combination of anilines, alkyl aldehydes, and phenylacetylene produces a range of 2-alkyl-quinolines. In addition to synthesis and purification, these new compounds are spectroscopically characterized by mass (MS), infrared (IR), and proton, carbon, and, if applicable, fluorine nuclear magnetic resonance (NMR). In vitro testing of these new target quinolines against lung cancer cell line A549 and glioma cell line GL26 is underway.