Synthesis of Molecules with Potential Biological Activity: A Social Justice Project in Chem 331L: Organic Chemistry II Lab
Faculty Sponsor
Gemma D'Ambruoso, Gonzaga University
Research Project Abstract
In past years, students in organic chemistry II lab (Chem 331L) at Gonzaga University have synthesized α,β-unsaturated ketones, commonly called chalcones, which can be reacted in Michael addition and aldol condensation reactions to make cyclohexenone molecules that could potentially display biological activity such as antibacterial properties. We aim to synthesize molecules similar to these, yet replacing one of the carbons in the ring with a nitrogen because nitrogen has better biological compatibility due in part to greater hydrophilicity. We were successful in synthesizing an intermediate in the synthesis, N-acetyl-4-methyl-benzamide, in high yield. The intermediate was then reacted with chalcones. Although we have signs of success, many side-products also appear to have been formed. Further purification and analysis should reveal whether or not the 5,6-dihydropyridin-2(1H) derivative was formed. When the desired product is formed and finally purified, we will then work with the microbiology lab (Biol 370) to test the moleculesantibacterial properties.
Session Number
PS2
Location
Graves Gym
Abstract Number
PS2-x
Synthesis of Molecules with Potential Biological Activity: A Social Justice Project in Chem 331L: Organic Chemistry II Lab
Graves Gym
In past years, students in organic chemistry II lab (Chem 331L) at Gonzaga University have synthesized α,β-unsaturated ketones, commonly called chalcones, which can be reacted in Michael addition and aldol condensation reactions to make cyclohexenone molecules that could potentially display biological activity such as antibacterial properties. We aim to synthesize molecules similar to these, yet replacing one of the carbons in the ring with a nitrogen because nitrogen has better biological compatibility due in part to greater hydrophilicity. We were successful in synthesizing an intermediate in the synthesis, N-acetyl-4-methyl-benzamide, in high yield. The intermediate was then reacted with chalcones. Although we have signs of success, many side-products also appear to have been formed. Further purification and analysis should reveal whether or not the 5,6-dihydropyridin-2(1H) derivative was formed. When the desired product is formed and finally purified, we will then work with the microbiology lab (Biol 370) to test the moleculesantibacterial properties.
