Browsing by Author "Ould Lamara, Kamilia"

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    Green synthesis, antioxidant and antibacterial activities of 4-aryl-3,4- dihydropyrimidinones/thiones derivatives of curcumin. Theoretical calculations and mechanism study
    (Elsevier, 2019) Khaldi-Khellafi, Nassima; Makhloufi-Chebli, Malika; Oukacha-Hikem, Djamila; Terachet Bouaziz, Souhila; Ould Lamara, Kamilia; Idir, Taous; Benazzouz-Touami, Amina; Dumas, Françoise
    3,4-Dihydropyrimidin-2(1H)-one/thione analogs of curcumin were synthesized in good yield by a onepot multi-component cyclocondensation using curcumin, substituted aromatic aldehydes, and urea/ thiourea in less volume of ethanol catalysed by commercial heteropolyacide Keggin type H3PMo12O40 5% mol as a recyclable and nontoxic catalyst under conventional heating and microwave irradiation. All the synthesized curcumin derivatives 4aen were screened for antioxidant and antimicrobial activity. Biological activity data of the synthesized showed that most of the synthesized compounds exhibited greater antioxidant and antibacterial activity than curcumin. Geometries of synthesized compounds were optimized by using B3LYP method with 6-31G* basis set. Then, DFT based reactivity descriptors such as HOMO, LUMO, chemical hardness, electronegativity, chemical potential were calculated and discussed.
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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
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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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    Synthesis, biological activities of chalcones and novel 4-acetylpyridine oximes, molecular docking of the synthesized products as acetylcholinesterase ligands
    (Elsevier, 2022) Ould Lamara, Kamilia; Makhloufi-Chebli, Malika; Benazzouz-Touami, Amina; Terrachet-Bouaziz, Souhila; Robert, Anthony; Machado-Rodrigues, Carine; Behr, Jean-Bernard
    Heterocyclic chalcones were synthesized by reaction of 4-acetylpyridine with the corresponding aromatic aldehydes under Claisen Schmidt conditions. These chalcones were used as starting material for the synthesis of oximes in the presence of hydroxylamine hydrochloride. The structures of the synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and ESI-MS, HRMS spectral analyses. All the synthesized compounds were evaluated for their antioxidant activity by DPPH• method and their in vitro antimicrobial activity by disk diffusion method against two Gram-negative bacteria, one Gram-positive bacteria and two fungal strains (C. albicans and A. niger). The results showed that the synthesized compounds did not display significant antioxidant activity. However, compounds 3b, 3d, 3f, 3h, 3i showed excellent antibacterial activity better than the standard drug against the bacterial strain S. aureus (ATCC 25923). The two compounds 3c, 3d proved very active against the fungal strain A. niger (MIC= 7.81 µg/ mL, 15.62 µg/mL respectively) while the antifungal drug used as reference (Fluconazole) was inactive. Molecular docking and molecular dynamics results revealed that the synthesized compounds, 4e, 4c, and 5j, were involved in a large number of favorable interactions with the active site residues of the acetylcholinesterase protein, which can stabilize the ligands in the active site and increase their affinities