Browsing by Author "Makhloufi-Chebli, Malika"

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Design, Synthesis, Biological evaluation of Isonicotinoyl-pyrazolyl-coumarin derivatives and computational study
(Elsevier, 2022) Halit, Sabrina; Benazzouz-Touami, Amina; Makhloufi-Chebli, Malika; TerrachetBouaziz, Souhila; Ighilahriz, Karima; Robert, Anthony; Machado-Rodrigues, Carine
A new series of 3-(5-Hydroxy-1-isonicotinoyl-3-methyl-4,5-dihydro-1H-pyrazol-5-yl)-2H-chromen-2-one derivatives 3a-g was efficiently synthesized under environmentally friendly reaction conditions by reaction of 3-acetoacetylcoumarin derivatives 1a-g with isoniazid 2. The reaction is conveniently performed at room temperature using Knorr pyrazole syntheses. The key features of this approach are its operational simplicity, the facile access to the desired products, and the good to excellent yields. The structures of the newly synthesized compounds were established by 1H, 13C, 2D NMR spectroscopy and mass spectrometry. 1H-15N HMBC experiments were also conducted to assess the regiochemistry of final compounds. All the synthesized compounds were evaluated for their in vitro antifungal activity against both Candida albicans and Aspergillus niger strains and compared to the standard drug Ketoconazole. Among all the compounds, 3d and 3e were the most effective, showing high potential antigungal inhibitory activities with respective MIC values of 15.62 µg ml−1 for 3e against Aspergillus niger. All the newly synthesized derivatives 3a-g are evaluated for their antioxidant activity and showed good activity. SAR studies demonstrated that the presence of nitro and hydroxyl groups in the aromatic ring of the coumarin and pyrazoline rings conferred enhanced antioxidant and antifungal activity. In addition, molecular docking studies were performed for compound 3e to evaluate its potential as an inhibitor of the fungal protein (Phytase A) from Aspergillus niger and the results suggested that our isonicotinoyl-pyrazolyl-coumarin may act as promising antifungal agent
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.
Green synthesis, characterization, structure, biological activity, theoretical calculations and drug-likeness analysis of coumarins
(Elsevier, 2020) Khaldi-Khellafi, Nassima; Oukacha-Hikem, Djamila; Terrachet Bouaziz, Souhila; Abdoun, Amar; Makhloufi-Chebli, Malika; Dumas, Françoise; M.S. Silva, Artur; Hamdi, Maamar
Condensation of salicylaldehydes and 2-hydroxynaphthaldehyde with various β−dicarbonyl derivatives 2a-c , in the presence of KF-Al 2 O 3 , leads to the synthesis of a series of coumarins 3-8 and benzo[ f ]coumarins 10 respectively by a solvent free reaction under microwave irradiation. The catalyst is recovered by a simple filtration and reused in subsequent reactions. The structure of all synthesized compounds has been established by using analytical techniques such as IR, 1 H and 13 C NMR spectroscopic spectra and elemental analysis. Most of the coumarins exhibited significant antibacterial activity against S. aureus Gram-positive bacteria compared to Cefotaxime as positive control. The compounds 4a and 7a demonstrated moderate antimicrobial activity against compound 8a is extremely sensitive.. In addition, the compounds showed moderate to good antiradical (DPPH) activity. Theoretical calculations let us to confirm the reaction mechanism. Parameters drug-likeness and physicochemical properties including pharmacokinetic analysis of the synthesized compounds was performed using DruliTo program.
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
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
Study of the novel fluorescent 4-methyl-9-(3-oxobutanoyl)-2H,8H-pyrano[2,3-f]chromene-2,8-dione derivative. estimation of the ground- and excited-state dipole moments from a solvatochromic shift
(Elsevier, 2017) Al-Kawkabani, Ahmed; Makhloufi-Chebli, Malika; Benosmane, Nadjib; Boutemeur-Kheddis, Baya; Hamdi, Maamar; Silva, Artur M.S.
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
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
Synthesis, characterization, theoretical studies, ADMET and drug- Likeness analysis: Electrochemical and biological activities of metal complexes of 3-(2-hydroxybenzoyl)-2H-chromen-2-one
(Elsevier, 2019) Belkhir-Talbi, Drifa; Makhloufi-Chebli, Malika; Terrachet-Bouaziz, Souhila; Hikem-Oukacha, Djamila; Ghemmit, Naima; Ismaili, Lhassane; M.S Silva, Artur; Maamar, Hamdi
Coordination compounds of 3-(2-hydroxybenzoyl)-2H-chromen-2-one were synthesized by the reaction of Cu(II), Co(II) and Zn(II) salts in molar ratio 1: 1 in basic media. The compounds formed were characterized using infrared, Uv–vis spectrophotometric analyses, mass spectrometry, elemental analyses and NMR spectroscopy. It was concluded that 3-(2-hydroxybenzoyl)-2H-chromen-2-one coordinated as a mono ligand for all the complexes; it also coordinated via the two carbonyl moieties. The electrochemical behavior of these compounds was determined by cyclic voltammetry. The synthesized compounds were screened for their antimicrobial and antioxidant activities. The complexes exhibited good antimicrobial activity against Staphylococcus aureus (ATCC 25923) and good antioxidant activity. Parameters drug-likeness and ADME properties are calculated.
Synthesis, DFT/TD-DFT theoretical studies, experimental characterization, electrochemical and antioxidant activity of Fe(III) complexes of bis (dimethylglyoximato) guanine
(Elsevier, 2019) Abane-Merzouk, Lamia; Adkhis, Ahmed; Terrachet-Bouaziz, Souhila; Makhloufi-Chebli, Malika
A new series of Iron (III) complexes of general formula [Fe(Hdmg) 2 (Gua)X]nH 2 O where (Hdmg = dimethylglyoximato monoanion, Gua = Guanine, X = Cl, Br or I) have been prepared and characterized by elemental analysis, conductivity, infrared spectra and electronic spectra. The molar conductance data confirm that all the complexes are no electrolytic. The mode of bonding and geometry of the Fe(III) complexes have been inferred spectral data, an octahedral geometry is ascribed for all the Fe(III) complexes. In these compounds, two dimethylglyoximato monoanions bond to the metal in the equatorial plan have been formed. The two axial sites being occupied by the guanine and the halogen moieties. The thermal properties of the Fe(III) complexes were investigated using TG and TDA. The thermal behavior of the compounds illustrates the general decomposition patterns of the complexes. The voltammetry experiments have been performed on the complexes to evaluate the redox process of Fe(III)/Fe(II) couple. These compounds were screened for their in-vitro antioxidant properties using 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.) free radical scavenging. The results obtained show that these complexes have a good antioxidant activity in comparison with ascorbic acid as positive control
Transition-metal complexes of N,N′-di(4-bromophenyl)-4-hydroxycoumarin-3-carboximidamide : synthesis, characterization, biological activities, ADMET and drug-likeness analysis
(Elsevier, 2021) Belkhir-Talbi, Drifa; Ghemmit-Doulache, Naima; Terrachet-Bouaziz, Souhila; Makhloufi-Chebli, Malika; Rabahi, Amal; Ismaili, Lhassane; Silva, Artur M.S.
Coordination compounds of N,N’-di(4-bromophenyl)-4-hydroxycoumarin-3-carboximidamide (L1) were synthesized via the reaction of Cu (II), Co (II) and Zn (II) salts in molar ratio 1 : 1 in the presence of ammoniac as basic media. The Ligands and the complexes formed were characterized using FT-IR, UV–visible and fluorescence spectrophotometric analyses, mass spectrometry, elemental analyses and NMR spectroscopy. It was concluded that N,N’-di(4-bromophenyl)-4-hydroxycoumarin-3-carboximidamide (L1) coordinated as a mono ligand for all the complexes; it also coordinated via the –OH and –NH groups. The electrochemical behaviour of these compounds was determined by cyclic voltammetry. The synthesized compounds were screened for their antimicrobial and antioxidant activities. All the complexes except that of copper show good activities against the S. aureus and those of cobalt and zinc have very interesting diameters of inhibition but lower antioxidant activity than the ligand L1. Parameters drug-likeness and ADMET (Absorption, Distribution, Metabolism, and Excretion) properties have been calculated