Preprint Article Version 1 This version is not peer-reviewed

Synthesis, X-ray Crystal Structures, Computational Studies and Catechol Oxidase Activity of New Acylhydrazone Derivatives

Version 1 : Received: 26 January 2018 / Approved: 28 January 2018 / Online: 28 January 2018 (12:44:49 CET)

How to cite: Karrouchi, K.; Radi, S.; El Bekkaye, Y.; Sebbar, N.K.; Taoufik, J.T.; Ouzidan, Y.; Ghabbour, H.A.; Mabkhot, Y.; Al-Showiman, S.; Alterary, S.; Ansar, M. Synthesis, X-ray Crystal Structures, Computational Studies and Catechol Oxidase Activity of New Acylhydrazone Derivatives. Preprints 2018, 2018010260 (doi: 10.20944/preprints201801.0260.v1). Karrouchi, K.; Radi, S.; El Bekkaye, Y.; Sebbar, N.K.; Taoufik, J.T.; Ouzidan, Y.; Ghabbour, H.A.; Mabkhot, Y.; Al-Showiman, S.; Alterary, S.; Ansar, M. Synthesis, X-ray Crystal Structures, Computational Studies and Catechol Oxidase Activity of New Acylhydrazone Derivatives. Preprints 2018, 2018010260 (doi: 10.20944/preprints201801.0260.v1).

Abstract

To make low-cost catalytic materials that mimic the activity of tyrosinase enzymes (Catechol oxidase) is an exciting challenge of biochemical technology. Herein, we report the synthesis of a series of acylhydrazone-pyrazoles based biomolecule materials (L1-L7) with superior catecholase activity. These biomolecules were synthesized by a one pot chemical condensation between 5-methyl-1H-pyrazole-3-carbohydrazide and benzaldehyde derivatives. The X-ray single crystal diffraction (XRD) for two ligands L1 and L2 have been studied and the molecular structures were optimized and confirmed using the density functional theory (DFT/B3LYP) method. Copper (II) complexes of the biomolecules (L1-L7), generated in-situ, and were studied for their catalytic activities towards the oxidation reaction of catechol to ortho-quinone according to two parameters: the nature of the ligand and the nature of counter anion. The L7-CuSO4 was found to have an excellent catalytic activity (105.42 μmol·L−1·min−1) among the catalysts recently reported in the existing literature.

Subject Areas

Acylhydrazone; Pyrazole; X-ray crystallography; DFT/B3LYP; Catecholase activity

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