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Investigation of the efficacy on tyrosinase enzyme of 5-substituted-1H-tetrazole derivatives synthesized with Pd-containing nanoparticle

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Abstract

Synthesis of 5-substituted-1H-tetrazole derivatives from aryl aldehydes under the influence of Palladium nanoparticles entrapped in aluminum hydroxide matrix (Pd/AlO(OH) NPs) was carried out in ethanol for 3-6 h. The use of the catalyst in this synthesis is the first. Sodium azide and malononitrile used in the reaction are chemical compounds required in the synthesis of tetrazoles. The reactions were concluded with good yields under thermal conditions. In the reactions, twelve derivatives were synthesized. The synthesized compounds were characterized by IR, 1H, and 13C NMR. The olefinic proton's signal, which is around 8.5 ppm, reveals the formation of the tetrazole ring. The tyrosinase enzyme activity for each synthesized derivative was examined, and the results were recorded. According to the results obtained, all tetrazole derivatives were found to be effective compounds for tyrosinase enzyme inhibition. 3-(3,4-dichlorophenyl)-2-(1H-tetrazol-5-yl)acrylonitrile (2k) with two chloride groups at the meta and para position of the phenyl ring seems to be the most potent tyrosinase inhibitor with an IC50 value of 45 µM.

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SYNOPSIS: 5-substituted-1H-tetrazole derivatives were synthesized under the influence of PdAlO(OH) NPs and under mild conditions. Tyrosinase enzyme activity was investigated for each of the twelve synthesized derivatives. As a result, synthesized tetrazole derivatives were identified as potential tyrosinase inhibitors.

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Acknowledgments

This research was supported by the Duzce University Research Fund (grant no. 2022.26.07.1280).

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Authors and Affiliations

  1. Department of Natural, Herbal and Cosmetic Products, Institute of Health Sciences, Düzce University, 81620, Düzce, Turkey

    Elif Aydinli

  2. Kaynasli Vocational College, Düzce University, 81900, Düzce, Turkey

    Elif Aydinli & Haydar Goksu

  3. Department of Chemistry, Faculty of Science, Çankırı Karatekin University, 18100, Çankırı, Turkey

    Zeyad Adil Hameed & Sevki Adem

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  1. Elif Aydinli
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Correspondence to Haydar Goksu.

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Aydinli, E., Hameed, Z.A., Goksu, H. et al. Investigation of the efficacy on tyrosinase enzyme of 5-substituted-1H-tetrazole derivatives synthesized with Pd-containing nanoparticle. J Chem Sci 136, 22 (2024). https://doi.org/10.1007/s12039-024-02254-w

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  • DOI: https://doi.org/10.1007/s12039-024-02254-w

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