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Synthesis of Novel N-Acylhydrazones Derived from 3,5-Dinitrobenzohydrazide and Evaluation of Their Anticholinesterase and Antioxidant Activities

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Abstract

Objective: In this study, it was aimed to determine the antioxidant activities and enzyme inhibition properties of newly synthesized N-acylhydrazone compounds (IIIa–IIIp) bearing an aryl sulfonate moiety. Methods: For this purpose, a series of hydrazone derivatives based on 3,5-dinitrobenzohydrazide (I) was synthesized for the first time and characterized by spectrometric methods (FT-IR, 1H NMR and 13C NMR) and elemental analysis. In vitro anticholinesterase activities of novel hydrazone derivatives were evaluated against acetyl- and butyrylcholinesterase (AChE and BChE) at 200 µM concentration. Moreover, the antioxidant potentials of the same molecules were determined by 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging activity and cupric ion reducing antioxidant capacity (CUPRAC) assays. Results: The obtained results displayed that some of the tested hydrazone compounds had varying enzyme inhibition and antioxidant activities. Discussion: In enzyme inhibition studies, N′-[2-{[4-fluorobenzensulfonyl]oxy}benzylidene]-3,5-dinitrobenzohydrazide (IIIb) with inhibition value 77.13 ± 0.14% showed the closest activity to the standard compound galanthamine with inhibition value 78.14 ± 0.65%. Compared to DPPH and ABTS assays, all of the molecules tested in CUPRAC assay showed antioxidant activities. The molecules tested in CUPRAC assay did not show as much activity as standard molecules (BHA, BHT and α-TOC). Conclusions: Compounds N′-[4-{[4-fluorobenzensulfonyl]oxy}benzylidene]-3,5-dinitrobenzohydrazide (IIIf) and N′-[4-{[4-methoxybenzensulfonyl]oxy}benzylidene]-3,5dinitrobenzohydrazide (IIIh) in this assay were determined to be the most active molecules.

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DATA AVAILABILITY

The data that support the findings of this study are available from the corresponding author upon reasonable request.

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Funding

This work was supported by the Scientific Research Projects Coordination Unit of Batman University (Grant no. BTÜBAP-2023-SBMYO-02).

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Authors and Affiliations

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

    Reşit Çakmak

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

    Ercan Çınar

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

    Eyüp Başaran

  4. Department of Medical Biology, Faculty of Medicine, Dicle University, 21280, Diyarbakır, Turkey

    Gülsüm Tuneğ

  5. Department of Medical Biology, Faculty of Medicine, Gaziantep University, 27410, Gaziantep, Turkey

    Sevcan İzgi

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

    Mehmet Boğa

  7. Dicle University Health Sciences Application and Research Center (DÜSAM), 21280, Diyarbakır, Turkey

    Mehmet Boğa

Authors
  1. Reşit Çakmak
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  2. Ercan Çınar
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  3. Eyüp Başaran
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  4. Gülsüm Tuneğ
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  5. Sevcan İzgi
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  6. Mehmet Boğa
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Contributions

The authors EB, RÇ—designed the experiments. The authors EB, RÇ, and EÇ—synthesized the chemical compounds. The author EB—elucidated the structures of the compounds using spectroscopic methods. The authors EÇ, MB, GT, and Sİ—carried out all stages of biological activity studies. The authors RÇ, EB—participated in the data processing and contributed to the preparation of the article.

All authors participated in the discussions.

Corresponding author

Correspondence to Eyüp Başaran.

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Informed consent was not required for this article. No conflict of interest was declared by the authors.

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Çakmak, R., Çınar, E., Başaran, E. et al. Synthesis of Novel N-Acylhydrazones Derived from 3,5-Dinitrobenzohydrazide and Evaluation of Their Anticholinesterase and Antioxidant Activities. Russ J Bioorg Chem 50, 76–85 (2024). https://doi.org/10.1134/S1068162024010114

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