Pyrazole Compounds : Synthesis, molecular structure, chemical reactivity, experimental and theoretical DFT FTIR spectra

Kaddouri, Yassine; Abrigach, Farid; Mechbal, N.; Karzazi, Y.; Kodadi, Mohamed El; Aouniti, A.; Touzani, Rachid

doi:10.1016/j.matpr.2019.04.060

Cited by 8 publications

(7 citation statements)

References 39 publications

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“…e title compounds (1-13) (Figure 1) were synthesized in one-pot condensation reaction following the known methodology described in literature [17][18][19][20][21][22].…”

Section: General Procedures For Synthesis Of Mono-and Tetra-alkylated Pyrazole and Triazole Ligandsmentioning

confidence: 99%

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Synthesis, Molecular Docking, MEP and SAR Analysis, ADME-Tox Predictions, and Antimicrobial Evaluation of Novel Mono- and Tetra-Alkylated Pyrazole and Triazole Ligands

Kaddouri

Bouchal

Abrigach

et al. 2021

Journal of Chemistry

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Newly synthesized compounds of N-alkylated heterocyclic compounds were prepared by condensation of amine with alcohol which undergoes a reaction of SN2. These newly synthesized derivatives were characterized by spectral analysis. The objective is to prepare new potent nontoxic antimicrobial agents which are easy to synthesize and could be scaled up in pharmaceutical industries. Thirteen new heterocyclic compounds containing a pyrazole moiety were synthesized with good yields (29.79 to 99.6%) and were characterized by FTIR, 1H NMR, 13C NMR, and CG-MS techniques. The compounds were divided into two series—monoalkylated compounds (1–11) and tetra-alkylated compounds (12 and 13)—and then evaluated for their in vitro antifungal and antibacterial activities against several fungal and bacterial strains. None of the monoalkylated compounds had antibacterial or antifungal activity. However, the two tetra-alkylated pyrazole ligands displayed strong antibacterial potential. Moreover, compound 12 was more potent against all tested bacterial strains than compound 13. Interestingly, compounds 12 and 13 acted as weak antifungal agents against Saccharomyces cerevisiae. ADME-Tox studies suggested that compounds 12 and 13 exhibit better toxicity profiles than the commercial antibiotic streptomycin. MEP studies suggested that compounds 12 and 13 have the same charge locations but differ in their values which are due to the condensed geometry of compound 13 that make it more polarizable than compound 12. Of particular interest, these different MEPs were evident in ligand protein docking, suggesting that compound 12 has better affinity with MGL enzyme than compound 13. All these findings suggested that these novel compounds represent promising antibacterial lead compounds.

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“…e title compounds (1-13) (Figure 1) were synthesized in one-pot condensation reaction following the known methodology described in literature [17][18][19][20][21][22].…”

Section: General Procedures For Synthesis Of Mono-and Tetra-alkylated Pyrazole and Triazole Ligandsmentioning

confidence: 99%

“…In context of fighting against these diseases, nitrogenous compounds have big interest either as antibacterial and/or antifungal agents. Particularly, pyrazole, triazole, benzotriazole, thiazole, imidazole, pyridine, and pyrimidine are very important moieties for the preparation of multiple interesting ligands [17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking, MEP and SAR Analysis, ADME-Tox Predictions, and Antimicrobial Evaluation of Novel Mono- and Tetra-Alkylated Pyrazole and Triazole Ligands

Kaddouri

Bouchal

Abrigach

et al. 2021

Journal of Chemistry

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“…The ligands 1-9, 11, and 12 were prepared by condensation of different monoamines with pyrazole or 1,2,4-triazole methanol derivatives (Pathway A, Figure 1), whereas 10 were prepared by condensation of imidazole with ethyl 1-(hydroxymethyl)-5-methyl-1H-pyrazole-3-carboxylate (Pathway B, Figure 1), according to the method described in the literature (Kaddouri et al, 2017(Kaddouri et al, , 2019(Kaddouri et al, , 2020.…”

Section: General Procedures For Preparing Compounds 1-12mentioning

confidence: 99%

“…The modeled proteins structure of Fophy considered as target reported in the literature (Abrigach et al, 2018;Kaddouri et al, 2019;Tighadouini et al, 2019;Toubi et al, 2019) was prepared in Autodock 4 default parameters, and the whole protein was used as grid for blind docking-virtual screening (Table 1) with Perl as launcher of virtual screening for all the ligands in Autodock Vina (Seeliger and de Groot, 2010).…”

Section: Protein Preparation and Active Site Selectionmentioning

confidence: 99%

“…The mono-alkylated ligands based on pyrazole and 1,2,4-triazole are prepared (Figure 2), whereas compounds 5, 6, 9, and 11 were described in the literature (Touzani et al, 2003;Kaddouri et al, 2019Kaddouri et al, , 2020. Several physicochemical analysis methods that are described in section Synthesis of the Pyrazole and Triazole Ligands characterized the prepared ligands.…”

Section: Chemistrymentioning

confidence: 99%

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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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One-pot solvent-free synthesis of 1,3,5-trisubstituted 1H-pyrazoles catalyzed by H3[PW12O40]/SiO2 under microwave irradiation

et al. 2022

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Pyrazole Compounds : Synthesis, molecular structure, chemical reactivity, experimental and theoretical DFT FTIR spectra

Cited by 8 publications

References 39 publications

Synthesis, Molecular Docking, MEP and SAR Analysis, ADME-Tox Predictions, and Antimicrobial Evaluation of Novel Mono- and Tetra-Alkylated Pyrazole and Triazole Ligands

Synthesis, Molecular Docking, MEP and SAR Analysis, ADME-Tox Predictions, and Antimicrobial Evaluation of Novel Mono- and Tetra-Alkylated Pyrazole and Triazole 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

One-pot solvent-free synthesis of 1,3,5-trisubstituted 1H-pyrazoles catalyzed by H3[PW12O40]/SiO2 under microwave irradiation

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