Heterocyclic Schiff base derivatives containing pyrazolone moiety: Synthesis, characterization, and in vitro biological studies

In this study, some pyrazolone-based Schiff base derivatives 2a-e (except 2a) were synthesized for the first time and structurally illuminated by some spectroscopic techniques (H-1, C-13 NMR, FT-IR) and elemental analysis. All synthesized molecules were screened for their anticancer and antioxidant activities, as well as AChE, BChE, and tyrosinase inhibitory properties. The obtained results exhibited that compounds 1b (IC50 = 9.497 mu M) and 2a (IC50 = 30.49 mu M) significantly decreased the proliferation of HeLa cells. On the other hand, the apoptotic effects of these two compounds were investigated with acridine orange/propidium iodide double staining. The apoptotic cell ratios of the molecules treated with these two compounds were determined as 60 and 64%. Compound 2b (IC50 = 17.95 +/- 0.47 mu M) was determined to be a very active substance in the ABTS assay. Compound 2e (A(0.5) = 43.75 +/- 0.62 mu M) indicated the closest antioxidant activity to the standard compound alpha-TOC (A(0.5) = 50.58 +/- 0.39 mu M) in the cupric reducing antioxidant capacity (CUPRAC) assay. In inhibition studies of enzymes, it was determined that compound 2c had a very active molecule in AChE, BChE, and tyrosinase inhibitory activities with 82.79 +/- 1.03, 91.39 +/- 1.06, and 92.60 +/- 1.80% inhibition, respectively. It was determined that the target molecules 2a-e showed better antioxidant and enzyme inhibitory activities than those of ester derivatives 1a-e.

Automated summary

Novel pyrazolone-based Schiff base derivatives were synthesized and evaluated for their anticancer, antioxidant, and enzyme inhibitory activities, showing potential pharmacological applications with significant antiproliferative effects against HeLa cells, as well as strong antioxidant and enzyme inhibitory properties.