Abstract

Combretastatin A-4 (CA-4) has long been used as an anti-mitotic agent; however, CA-4 is not a favorable drug for use in anti-cancer treatments, due to its high solubility in fats and its low solubility in aqueous media. Chalcones, which are derivatives of CA-4, have been found to have anti-bacterial and anti-cancer responses and can be further modified into various heterocyclic compounds. In this study, derivatives of the nitrogenous heterocyclic compound, pyrazoline, are the focus. Previous research has shown pyrazoline derivatives to be effective against various cancer cell lines. These molecules can be synthesized from the cyclization of chalcones by using an aryl aldehyde, along with hydrazine hydrate. Specifically, this project is concerned with the aza-Michael addition of hydrazine to synthesize pyrazoline derivatives using a “solvent free” method using the ionic liquid, [DBU][Ac] (1,8-diazabicyclo[5.4.0]- undec7-en-8-ium acetate). The use of [DBU][Ac] has been proven to be a good catalyst for aza-Michael addition reactions and can provide high yields. Three aza-Michael addition reactions have been attempted. However, all three syntheses resulted in a hydrazone byproduct, confirmed by comparison to the 1HNMR of a previously synthesized hydrazone. In addition, chalcone, [DBU][Ac], and benzylamine were reacted in order to gain more insight on the reactivity of the chalcone.

How to Cite