Abstract

Synthesis of pyrazoline derivatives has been an active field of research due to the established biological and pharmaceutical activities of these compounds such as antibacterial, anti-inflammatory, and anticancer properties. Pyrazoline derivatives can be produced from the cyclization of chalcones with hydrazine hydrate and an aryl aldehyde. The goal of this project is aza-Michael addition of aliphatic amines to various α,β unsaturated carbonyl compounds as a novel approach for pyrazoline synthesis using ionic solvents. Previous research has proven that the use of DBU (1,8-diazabicyclo[5.4.0]-undec7-ene-8) as a catalyst/promoter for aza-Michael addition can provide high yields and has the additional advantage of good reusability. However, the “one pot” total synthesis of pyrazoline derivatives has proven to produce low yields. In this project, the reaction between chalcone (1A-E), hydrazine hydrate, and benzaldehyde with [DBU][Ac] (1,8-diazabicyclo[5.4.0]-undec7-en-8-ium acetate) acting as a catalyst was found to successfully synthesize various pyrazoline derivatives (2A-H). Compounds 2A-D were tested for their biological activity through a series of bioassays (MTT, Cell Death, and XTT). All four compounds possessed both anticancer and antibiotic activity. Compound 2D was found to possess activity comparable to Vancomyocin, a known antibiotic, against gram-positive bacteria. This finding supports the notion that methoxy groups enhance bioactivity. However, further research will need to be completed to test the activity of all pyrazoline derivatives in order to confidently state any trends among biological activity and substituents.

How to Cite