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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 (1H, 13C 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 μΜ) and 2a (IC50 = 30.49 μΜ) 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 μΜ) was determined to be a very active substance in the ABTS assay. Compound 2e (A0.5 = 43.75 ± 0.62 μM) indicated the closest antioxidant activity to the standard compound α‐TOC (A0.5 = 50.58 ± 0.39 μM) 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. [ABSTRACT FROM AUTHOR]

In this research work, a series of heterocyclic Schiff base compounds bearing arylsulfonyl ester moiety (2a-i) were designed, synthesized, characterized by spectral techniques such as 1D NMR (¹H and 13C), 2D NMR (COSY and HMQC), and FT-IR; and then examined their antioxidant activity was by using four different methods as DPPH, ABTS, CUPRAC, and β-carotenelinoleic acid assays. According to the results obtained, it determined that all synthesized molecules had antioxidant activity. In the DPPH assay, it was found that compound 2e (IC50: 96.23±0.02 μM/mL) demonstrated the antioxidant activity among all synthesized molecules. In ABTS assay, compounds 2e (IC50: 41.88±0.21 μM/mL) and 2g (IC50: 50.75±0.32 μM/mL) were determined to be the molecules with the activity, respectively. Compound 2e (IC50:73.49±0.00 μM/mL) indicated the best antioxidant activity in the CUPRAC assay compared to other synthesize molecules. In the β-carotene-linoleic acid assay, compound 2e (IC50: 58.79±0.58 μM/mL) displayed antioxidant activity than all other synthesized molecules. Compounds 2d (IC50: 74.17±0.22 μM/mL) and 2g (IC50: 66.06±0.13 μM/mL) indicated higher antioxidant activity than the remaining molecules in this series, except for compound 2e. In conclusion, it is thought that this study will contribute to the ongoing studies on the design and synthesis of new antioxidant agents. [ABSTRACT FROM AUTHOR]