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Heterocyclic Schiff base derivatives containing pyrazolone moiety: Synthesis, characterization, and in vitro biological studies
Author(s) -
Çınar Ercan,
Başaran Eyüp,
Erdoğan Ömer,
Çakmak Reşit,
Boğa Mehmet,
Çevik Özge
Publication year - 2021
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.202100357
Subject(s) - chemistry , tyrosinase , hela , antioxidant , schiff base , moiety , pyrazolone , kojic acid , acetamide , carbon 13 nmr , stereochemistry , molecule , in vitro , nuclear chemistry , enzyme , organic chemistry , biochemistry
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 ( 1 H, 13 C 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 (IC 50 = 9.497 μΜ) and 2a (IC 50 = 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 (IC 50 = 17.95 ± 0.47 μΜ) was determined to be a very active substance in the ABTS assay. Compound 2e (A 0.5 = 43.75 ± 0.62 μM) indicated the closest antioxidant activity to the standard compound α ‐TOC (A 0.5 = 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 .