INVESTIGATION OF ANTIOXIDANT AND ANTI-ALZHEIMER PROPERTIES OF NOVEL 4-AMINOANTIPYRINE-DERIVED SCHIFF BASES

Authors : Ercan Çınar

Pages : 707-722

Doi:10.33715/inonusaglik.1642420

View : 44 | Download : 52

Publication Date : 2025-10-16

Article Type : Research Paper

Abstract :In this study, Schiff bases derived from 4-aminoantipyrine (4AAP) were synthesized and elucidated using spectroscopic methods (¹H- and ¹³C-NMR). DPPH (1,1-diphenyl-2-picrylhydrazyl) free radical scavenging test, 2,2\\\'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical scavenging activity, and copper ion reducing antioxidant capacity (CUPRAC) analysis were used to evaluate Schiff bases’ antioxidant potentials. Furthermore, their inhibitory potentials against cholinesterase (ChE) enzymes were investigated. The compound (4E)-4-(5-chloro-2-hydroxybenzylideneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (R3) exhibited a higher inhibition effect with an inhibitory value of 27.05 ± 0.13 µM as compared to the standard inhibitor neostigmine (33.3 ± 0.32 µM). The synthesized compounds were subjected to antioxidant tests, including DPPH, ABTS, and CUPRAC, respectively. In the DPPH experiment, the compound (4E)-4-(2-hydroxy-5-nitrobenzylideneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (R5) exhibited activity with a value of 116.79 ± 2.73 µM. However, in this test, all compounds showed lower antioxidant activity as compared to standard antioxidants such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), and α-tocopherol (α-TOC). By contrast, in the ABTS assay, all compounds were active as compared to standard antioxidants, and the R3 compound showed high antioxidant activity. In the CUPRAC experiment, although the compounds showed antioxidant activity, it was not as high as that of the standard antioxidants. (4E) -4-(2-hydroxybenzylideneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (R1) compound was the most effective in the CUPRAC method.
Keywords : 4-aminoantipirin, Alzheimer hastalığı, Antioksidanlar, Schiff bazı

ORIGINAL ARTICLE URL