Design, Synthesis and Biological Activities of Chalcones with Piperonal Moiety

Abstract

Heterocyclic compounds are of specific significance between pharmacologically active compounds. In this study, some piperonal-based chalcones (PC1-PC10) were synthesized with Claisen-Schmidt Condensation with the reaction between 3,4-methylenedioxybenzaldehyde and several acetophenones. Inhibition potency of the chalcones were evaluated toward human carbonic anhydrase I and II enzymes (hCA I and hCA II), and acetylcholinesterase (AChE). The chalcone derivatives were found to have IC50 values in the range of 5.11-109.70 μM for hCA I, 17.05-162.59 μM for hCA II, and 18.52-98.69 μM for AChE. All compounds showed lower inhibition potential than reference compounds. While the PC3 (methoxy derivative) compound was the most effective compound against both hCA I and hCA II, PC5 (fluorine derivative) showed the strongest inhibition effect against AChE in the series. Results confirmed that the chalcone derivatives PC3 and PC5 can be considered as favorable candidates against hCA I, hCA II and AChE isoenzymes to design more potent enzyme inhibitors.