Publications Scientifiques

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Author: search.filters.author.Terrachet-Bouaziz, SouhilaSubject: search.filters.subject.Antioxidant activity

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    Sodium dodecyl benzene sulfonate-catalyzed reaction for green synthesis of biologically active benzylpyrazolyl-coumarin derivatives, mechanism studies, theoretical calculations
    (Elsevier, 2022) Halit, Sabrina; Benazzouz-Touami, Amina; Makhloufi-Chebli, Malika; Terrachet-Bouaziz, Souhila; Ighil Ahriz, Karima
    In the present work, a multicomponent protocol has been described for the synthesis of various benzylpyrazolyl-coumarin 5a-i structures, involving the reaction of 4-hydroxycoumarin, ethyl acetoacetate, hydrazine hydrate, and aldehydes, using an ethanol-water (1:1) mixture as the reaction medium and sodium dodecylbenzenesulfonate (SDBS) as the catalyst. This new approach has advantages such as short reaction time, recovery of the catalysts after the catalytic reaction and their reuse without loss of activity, as well as the lightening of the process. The structures of the obtained benzylpyrazolylcoumarins were determined and confirmed by melting point, 1H NMR and 13C NMR. The determination of antioxidant activity of the obtained benzylpyrazolylcoumarin 5a-i derivatives was studied using the DPPH scavenging assay. Molecular modeling studies using DFT (density function theory) calculations showed that there are six tautomeric structures A to F in which structure C is more stable than the others
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    Synthesis, biological activities and molecular docking study of 3-(3-oxobutanoyl)-2H-chromen-2-one derivative
    (Elsevier, 2021) Benazzouz-Touami, Amina; Hikem-Oukacha, Djamila; Ould Lamara, Kamilia; Halit, Sabrina; Terrachet-Bouaziz, Souhila; Makhloufi-Chebli, Malika
    Herein, we report the highly efficient total synthesis of a series of 3-(3-oxobutanoyl)-2H-chromen-2-one derivatives from salicylaldehyde(s) and 4‑hydroxy-6-methyl-2H-pyran-2-one (TAL) using Na2S2O3 as green and efficient catalyst. Structure elucidation of the products has been accomplished based on FT-IR, mass spectroscopy, 1H NMR and 13C NMR spectroscopy. The in vitro antioxidant activities of the drugs 3-(3-oxobutanoyl)-2H-chromen-2-one were tested by the quantitative 1,1-diphenyl-2-picrylhydrazyl (DPPH.) radical scavenging activity method. The compounds 3b, 3c and 3e proved to be the most active, showing high capacity to deplete the DPPH radicals. All synthesized compounds were screened for their antimicrobial activities and the results show that only 3f was active against bacteria Staphylococcus aureus compared to antibiotic used as reference. In addition, all synthesized compounds were docked with FtsZ from S. aureus protein using AutoDock 4 software. The results suggest that 3f binds with FtsZ protein with lower energy and undergoes good interactions with the active site amino
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    Selectivity control in the reaction between 2-hydroxyarylaldehydes and 4-hydroxycoumarin. Antioxidant activities and computational studies of the formed products
    (Elsevier, 2021) Ould Lamara, Kamilia; Makhloufi-Chebli, Malika; Benazzouz-Touami, Amina; Terrachet-Bouaziz, Souhila; Hamdi, Nejla; Silva, Artur M.S.; Behr, Jean-Bernard
    A series of 6H,7H-7-(4-Hydroxy-3-coumarinyl)[1]benzopyrano[4,3-b][1]benzopyran-6-ones 4a-g and 3-(2-hydroxybenzoyl)-2H-chromen-2-ones 5a-g derivatives were synthesized by reaction of 4-hydroxycoumarin with 2-hydroxyarylaldehydes 2a-f or 2-hydroxynaphtaldehyde 2g using different solvents and acid/base catalysts. The approach relies on a regioselective cascade reaction involving one/two molar equiv of the 4-hydroxy coumarin iteratively acting as active methylene substrate in a Knoevenagel condensation and in a Michael addition. The structures of all compounds were established by IR, mass spectrometry, 1H-NMR and 13C-NMR. Antioxidant activity of the synthesized compounds were determined using the DPPH scavenging assay, best results being obtained with 5b (IC50 = 236 µg/mL). Computational studies showed that the compounds bind in the ATP-binding site of p38 MAPK, in a same manner than known polyaromatic potent inhibitors. The synthesized compounds might be considered further for cancer therapy