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Int. J. Mol. Sci. 2017, 18(11), 2215; https://doi.org/10.3390/ijms18112215

New Pyrazole-Hydrazone Derivatives: X-ray Analysis, Molecular Structure Investigation via Density Functional Theory (DFT) and Their High In-Situ Catecholase Activity

1
Laboratoire de Chimie Thérapeutique, Faculté de Médecine et de Pharmacie, Université Mohammed V, P. O. Box 8007, Rabat 10100, Morocco
2
Laboratoire de Chimie Appliquée et Environnement (LCAE), Faculté des Sciences, Université Mohamed I, P. O. Box 524, Oujda 60000, Morocco
3
Laboratoire National de Contrôle des Médicaments, Direction du Médicament et de la Pharmacie, Ministère de la Santé, P. O. Box 6206, Rabat 10100, Morocco
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Institution Supérieure des Professions Infirmières et Techniques de Santé, P. O. Box 4806, Oujda 60000, Morocco
5
Laboratoire de Chimie Organique Hétérocyclique, Pharmacochimie, Faculté des sciences, Université Mohammed V, P. O. Box 8007, Rabat 10100, Morocco
6
Laboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdellah, P. O. Box 2202, Fès 30000, Morocco
7
Department of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
8
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia
*
Authors to whom correspondence should be addressed.
Received: 18 September 2017 / Revised: 16 October 2017 / Accepted: 21 October 2017 / Published: 25 October 2017
(This article belongs to the Section Molecular Biophysics)
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Abstract

The development of low-cost catalytic systems that mimic the activity of tyrosinase enzymes (Catechol oxidase) is of great promise for future biochemistry technologic demands. Herein, we report the synthesis of new biomolecules systems based on hydrazone derivatives containing a pyrazole moiety (L1L6) with superior catecholase activity. Crystal structures of L1 and L2 biomolecules were determined by X-ray single crystal diffraction (XRD). Optimized geometrical parameters were calculated by density functional theory (DFT) at B3LYP/6–31G (d, p) level and were found to be in good agreement with single crystal XRD data. Copper (II) complexes of the compounds (L1L6), generated in-situ, were investigated for their catalytic activities towards the oxidation reaction of catechol to ortho-quinone with the atmospheric dioxygen, in an attempt to model the activity of the copper containing enzyme tyrosinase. The studies showed that the activities depend on four parameters: the nature of the ligand, the nature of counter anion, the nature of solvent and the concentration of ligand. The Cu(II)-ligands, given here, present the highest catalytic activity (72.920 μmol·L−1·min−1) among the catalysts recently reported in the existing literature. View Full-Text
Keywords: pyrazole; hydrazone; crystal structure; DFT; catecholase activity pyrazole; hydrazone; crystal structure; DFT; catecholase activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Karrouchi, K.; Yousfi, E.B.; Sebbar, N.K.; Ramli, Y.; Taoufik, J.; Ouzidan, Y.; Ansar, M.; Mabkhot, Y.N.; Ghabbour, H.A.; Radi, S. New Pyrazole-Hydrazone Derivatives: X-ray Analysis, Molecular Structure Investigation via Density Functional Theory (DFT) and Their High In-Situ Catecholase Activity. Int. J. Mol. Sci. 2017, 18, 2215.

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