Catechol oxidase and Copper(I/II) Complexes Derived from Bipyrazol Ligand: Synthesis, Molecular Structure Investigation of New Biomimetic Functional Model and Mechanistic Study

Ati, R. El; Takfaoui, Abdelilah; Kodadi, Mohamed El; Touzani, Rachid; Yousfi, El Bekkaye; Almalki, Faisal A.; Hadda, Taïbi Ben

doi:10.1016/j.matpr.2019.04.092

Cited by 10 publications

(7 citation statements)

References 12 publications

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Section: Resultsmentioning

confidence: 99%

“…Based on geometrical, physicochemical parameters of each site and electronic charge repartition of the corresponding X, Y, and Z heteroatoms (Sogabe et al, 2013;El Ati et al, 2019;ELMeskini et al, 2019;Guerf et al, 2020;Rachedi et al, 2020;Titi et al, 2019;Rad et al, 2017 andPezzuto et al, 1991). The analysis of conformations and the calculation of the atomic charge shown in Figures 8, 9, of the tested compounds are quite helpful in predicting the efficiency of a drug to the target interaction and, simultaneously, gaining insight into the drug potency and postulate about the favorable conformation of a drug and the antibacterial/ antitumor pharmacophore sites.…”

Section: Identification Of Pharmacophore Sitesmentioning

confidence: 99%

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Novel saccharin analogs as promising antibacterial and anticancer agents: synthesis, DFT, POM analysis, molecular docking, molecular dynamic simulations, and cell-based assay

et al. 2022

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Saccharine is a pharmacologically significant active scaffold for various biological activities, including antibacterial and anticancer activities. Herein, saccharinyl hydrazide (1) was synthesized and converted into 2-[(2Z)-2-(1,1-dioxo-1,2-dihydro-3H-1λ6,2- benzothiazole-3-ylidene) hydrazinyl] acetohydrazide (5), which was employed as a key precursor for synthesizing a novel series of small molecules bearing different moieties of monosaccharides, aldehydes, and anhydrides. Potent biological activities were found against Staphylococcus and Escherichia coli, and the results indicated that compounds 6c and 10a were the most active analogs with an inhibition zone diameter of 30–35 mm. In cell-based anticancer assay over Ovcar-3 and M-14 cell lines, compound 10a was the most potent analog with IC50 values of 7.64 ± 0.01 and 8.66 ± 0.01 µM, respectively. The Petra Orisis Molinspiration (POM) theoretical method was used to calculate the drug score of tested compounds and compare them with their experimental screening data. Theoretical DFT calculations were carried out in a gas phase in a set of B3LYP 6-311G (d,p). Molecular docking studies utilizing the MOE indicated the best binding mode with the highest energy interaction within the binding sites. The molecular docking for Ovcar-3 was carried out on the ovarian cancer protein (3W2S), while the molecular docking for M-14 melanoma was carried out on the melanoma cancer protein (2OPZ). The MD performed about 2ns simulations to validate selected compounds’ theoretical studies.

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Section: Resultsmentioning

confidence: 99%

Section: Identification Of Pharmacophore Sitesmentioning

confidence: 99%

Novel saccharin analogs as promising antibacterial and anticancer agents: synthesis, DFT, POM analysis, molecular docking, molecular dynamic simulations, and cell-based assay

et al. 2022

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“…The pyrazole derivatives ( Figure 9 ) investigated in this work were prepared following the experimental procedure of the N -alkylation reaction described previously in the literature [ 43 , 46 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 ]. First, all the compounds were prepared by condensation of primary amines with (3,5-dimethyl- 1H -pyrazole-1-yl)methanol or ( 1H -pyrazole-1-yl)methanol in acetonitrile as a polar aprotic solvent that promotes SN2 reaction; after that, the compounds were purified either by diethyl ether or a DCM:water (3:1) mixture to obtain the final products, with yields varying from 15.22 to 99.41%.…”

Section: Methodsmentioning

confidence: 99%

New N-Alkylated Heterocyclic Compounds as Prospective NDM1 Inhibitors: Investigation of In Vitro and In Silico Properties

et al. 2022

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A new family of pyrazole-based compounds (1–15) was synthesized and characterized using different physicochemical analyses, such as FTIR, UV-Visible, 1H, 13C NMR, and ESI/LC-MS. The compounds were evaluated for their in vitro antifungal and antibacterial activities against several fungal and bacterial strains. The results indicate that some compounds showed excellent antibacterial activity against E. coli, S. aureus, C. freundii, and L. monocytogenes strains. In contrast, none of the compounds had antifungal activity. Molecular electrostatic potential (MEP) map analyses and inductive and mesomeric effect studies were performed to study the relationship between the chemical structure of our compounds and the biological activity. In addition, molecular docking and virtual screening studies were carried out to rationalize the antibacterial findings to characterize the modes of binding of the most active compounds to the active pockets of NDM1 proteins.

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“…The compounds L 1 -L 4 (Figure 1) were synthesized following the reaction described in the literature (Kaddouri et al, 2020;Abrigach et al, 2018;El Kodadi et al, 2008;Touzani et al, 2011;Hammouti et al, 2012;Boussalah et al, 2013;Abrigach et al, 2016;Abrigach et al, 2017;Kaddouri et al, 2019;El Ati et al, 2019;Bouchal et al, 2019), where the L1 is synthesized by condensation of (4H-1,2,4-triazol-4-yl)methanol with 1Himidazole, L2 by condensation diethyl oxalate with propan-2-one (acetone), L3 is synthesized by condensation of ethyl 1-(hydroxymethyl)-5-methyl-1H-pyrazole-3carboxylate and 1H-imidazole and L4 is synthesized by condensation of ethyl 1-(hydroxymethyl)-5-methyl-1H-pyrazole-3carboxylate with ethyl 5-methyl-1Hpyrazole-3-carboxylate. All the studied compounds were purified either in acetonitrile or dichloromethane to obtain the final products with good yields.…”

Section: Compounds Synthesismentioning

confidence: 99%

Study of the Catecholase Activity of new catalysts Based on Copper (II) and Heterocyclic Ligands

Ati

Bouammali

Kodadi

et al. 2021

Indonesian J. Sci. Technol

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In this work, we are interested in finding new catalysts for catecholase, whose principle is based on the oxidation reaction of catechol to o-quinone. We approached the synthesis of the threes tripod ligands based on pyrazole in a condensation reaction and its characterization by IR, 13C NMR, 1H NMR spectroscopy, then we evaluated the catalytic properties of certain complexes formed in situ to catalyze the oxidation reaction of catechols to o-quinones. The aim is to find the right models to reproduce the catalytic activity of the enzyme (catecholase), we used complexes formed in situ by pyrazole derivatives with Copper salts. Among these complexes, the complex L4/Cu(CH3COO)2 showed good catalytic activity of the combination (1ligand/2metal) in MeOH for this reaction, with a speed Vmax equal to 69.38 μmol.L-1.min-1 and a low value of Km equal to 0.019 mol.L-1. We have demonstrated that the nature of concentration, ligand, solvent, and copper salts, influenced strongly the catecholase activity.

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Catechol oxidase and Copper(I/II) Complexes Derived from Bipyrazol Ligand: Synthesis, Molecular Structure Investigation of New Biomimetic Functional Model and Mechanistic Study

Cited by 10 publications

References 12 publications

Novel saccharin analogs as promising antibacterial and anticancer agents: synthesis, DFT, POM analysis, molecular docking, molecular dynamic simulations, and cell-based assay

Novel saccharin analogs as promising antibacterial and anticancer agents: synthesis, DFT, POM analysis, molecular docking, molecular dynamic simulations, and cell-based assay

New N-Alkylated Heterocyclic Compounds as Prospective NDM1 Inhibitors: Investigation of In Vitro and In Silico Properties

Study of the Catecholase Activity of new catalysts Based on Copper (II) and Heterocyclic Ligands

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