Antifungal activities of amino acid ester functional pyrazolyl compounds against Fusarium oxysporum f.sp. albedinis and Saccharomyces cerevisiae yeast

Boussalah, Nouria; Touzani, Rachid; Souna, Faiza; Himri, Iman; Bouakka, Mohammed; Hakkou, Abdelkader; Ghalem, Saïd; Kadiri, Sghir El

doi:10.1016/j.jscs.2011.02.016

Cited by 15 publications

(10 citation statements)

References 47 publications

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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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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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“…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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“…The selected compounds are all the testes against F.o.a., collected from the references (Waring et al, 2002;Radi et al, 2012Radi et al, , 2015Smaail et al, 2012;Boussalah et al, 2013;Loth et al, 2015;Abrigach et al, 2017Abrigach et al, , 2018Tighadouini et al, 2018Tighadouini et al, , 2019Koudad et al, 2019;Toubi et al, 2019).…”

Section: Dataset Preparationmentioning

confidence: 99%

Mono-Alkylated Ligands Based on Pyrazole and Triazole Derivatives Tested Against Fusarium oxysporum f. sp. albedinis: Synthesis, Characterization, DFT, and Phytase Binding Site Identification Using Blind Docking/Virtual Screening for Potent Fophy Inhibitors

et al. 2020

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Twelve recent compounds, incorporating several heterocyclic moieties such as pyrazole, thiazole, triazole, and benzotriazole, made in excellent yield up to 37–99.6%. They were tested against Fusarium oxysporum f. sp. albedinis fungi (Bayoud disease), where the best results are for compounds 2, 4, and 5 with IC50 = 18.8–54.4 μg/mL. Density functional theory (DFT) study presented their molecular reactivity, while the docking simulations to describe the synergies between the trained compounds of dataset containing all the tested compounds (57 molecules) and F. oxysporum phytase domain (Fophy) enzyme as biological target. By comparing the results of the docking studies for the Fophy protein, it is found that compound 5 has the best affinity followed by compounds 2 and 4, so there is good agreement with the experimental results where their IC50 values are in the following order: 74.28 (5) < 150 (2) < 214.10 (4), using Blind docking/virtual screening of the homology modeled protein and two different tools as Autodock Vina and Dockthor web tool that gave us predicted sites for further antifungal drug design.

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Antifungal activities of amino acid ester functional pyrazolyl compounds against Fusarium oxysporum f.sp. albedinis and Saccharomyces cerevisiae yeast

Cited by 15 publications

References 47 publications

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

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

Mono-Alkylated Ligands Based on Pyrazole and Triazole Derivatives Tested Against Fusarium oxysporum f. sp. albedinis: Synthesis, Characterization, DFT, and Phytase Binding Site Identification Using Blind Docking/Virtual Screening for Potent Fophy Inhibitors

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