Design and Synthesis of 2-Methyl Tryptamine-Maleimide Hybrids as a Potential Antitubercular Agents

Abstract

Over 2.8 million antibiotic-resistant infections occur every year in the United States. Of these infections, drug-resistant tuberculosis is of particular concern, especially for multi-drug resistant strains. Hybridization is a novel way to synthesize antibacterial drugs with unique mechanisms of action. 2-Methyl tryptamine and 3,4-diaryl maleimide structures were selected for hybridization based on previous research demonstrating their biological activity against tuberculosis. In this study, an optimized route was found to effectively synthesize pure 2-methyl tryptamine by modifying procedures from published literature. The reaction time and rate of addition of 5-chloro-2-pentanone were manipulated to produce a pure 2-methyl tryptamine to be used for hybridization. 3,4-diaryl maleimide structures were synthesized based on previous research in the lab. With the synthesis of each component, 8 maleimide-2-methyl tryptamine hybrids were successfully synthesized (52-122% yield) and 4 were purified (21-47% yield).