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Schiff Base Derivatives of 4-Aminoantipyrine as Promising Molecules: Synthesis, Structural Characterization, and Biological Activities

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Abstract

In this study, some Schiff bases derived from 4-aminoantipyrine (4-AAP) (VI–X) were synthesized, characterized by elemental analysis (C, H, N) and three spectral techniques (FT-IR, 1H, and 13C NMR), and then their antioxidant activity was investigated by employing four different methods. Subsequently, the inhibitory influences of the synthesized molecules against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), tyrosinase enzymes were tested. More importantly, the cytotoxic effects of all title molecules were also evaluated on HeLa human cervical cancer and L929 mouse fibroblast cell lines. According to the results obtained, compound (VI) (IC50: 16.82 ± 0.17 μM) showed higher ABTS cation radical scavenging activity than BHA (IC50: 17.59 ± 0.10 μM). In CUPRAC assay, it was determined that the activity ordering of the bioactive molecules has been determined as VII > X > VII > α-TOC > IX > I > II > V > VI. In AChE assay, compound (I) indicated a high potent inhibition activity with 91.75 ± 1.15% better than galanthamine. In BChE assay, compound (VII) had good BChE inhibition activity (78.76 ± 1.47%) better than galanthamine. Compound (V) showed strong tyrosinase inhibition activity with 52.85 ± 0.23% value at 200 μM concentration. Compound (III) showed the best cytotoxic effect on HeLa cells with an IC50 dose of 21.47 µM. Consequently, it can be said that some of these synthesized molecules were potentially new anti-Alzheimer drug candidate molecules.

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Authors and Affiliations

  1. Medical Laboratory Techniques Program, Vocational School of Health Services, Batman University, Batman, 72000, Turkey

    Reşit Çakmak

  2. Department of Chemistry and Chemical Processing Technologies, Vocational School of Technical Sciences, Batman University, Batman, 72000, Turkey

    Eyüp Başaran

  3. Department of Analytical Chemistry, Faculty of Pharmacy, Dicle University, Diyarbakır, 21280, Turkey

    Mehmet Boğa

  4. Department of Biochemistry, Faculty of Medicine, Adnan Menderes University, Aydın, 09010, Turkey

    Ömer Erdoğan & Özge Çevik

  5. Department of Nursing, Faculty of Health Sciences, Batman University, Batman, 72000, Turkey

    Ercan Çınar

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  1. Reşit Çakmak
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Reşit Çakmak, Başaran, E., Boğa, M. et al. Schiff Base Derivatives of 4-Aminoantipyrine as Promising Molecules: Synthesis, Structural Characterization, and Biological Activities. Russ J Bioorg Chem 48, 334–344 (2022). https://doi.org/10.1134/S1068162022020182

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