Publications internationales

K. Otmane Rachedi, R. Bahadi, B. Belhani, A. Bouzina, M. Aissaoui, T. Ben Hadda, M. Berredjem. (2020), DFT Study, POM Analyses and Molecular Docking of Novel Oxazaphosphinanes: Identification of Antifungal Pharmacophore Site. Indonesian Journal of Chemistry

Résumé: A computational Petra/Osiris/Molinspiration/DFT(POM/DFT) based model has been developed for the identification of physico-chemical parameters governing the bioactivity of series of oxazaphosphinanes derivatives 1a-1f containing potential antifungal O,N-pharmacophore. Molecular docking study was performed in order to evaluate synthesized compounds their possible antifungal properties and their interactions in the binding site. Molecular docking studies revealed that the compounds 1a-1f have the potential to become lead molecules in the drug discovery process. The six compounds 1a–1f analyzed here were previously synthesized by our group.

S.Haidar, C.Marminon, D.Aichele, A.Nacereddine, W.Zeinyeh, A.Bouzina, M.Berredjem, L.Ettouati, Z. Bouaziz, M. Le Borgne, J.Jose. (2020), QSAR Model of Indeno [1, 2-b] indole Derivatives and Identification of N-isopentyl-2-methyl-4, 9-dioxo-4, 9-Dihydronaphtho [2, 3-b] furan-3-carboxamide as a Potent CK2 Inhibitor. Molecules
K.Bechlem, M.Aissaoui, B.Belhani, K.Otmane Rachedi, S.Bouacida, R.Bahadi, S.Djouad, R.Ben Mansour, M.Bouaziz, F.Almalki, T.Ben Hadda, M.Berredjem. (2020), Synthesis, X-ray crystallographic study and molecular docking of new -sulfamidophosphonates: POM analyzes of their cytotoxic activity. Journal of Molecular Structure
Ismahene Grib, Malika Berredjem, Khadidja Otmane Rachedi, Seif-Eddine Djouad, Sofiane Bouacida, Rania Bahadi, Tan-Sothea Ouk, Mekki Kadri, Taibi Ben Hadda, Billel Belhani. (2020), Novel N-sulfonylphthalimides: Efficient synthesis, X-ray characterization, spectral investigations, POM analyses, DFT computations and antibacterial activity. Molecular structurejournal homepage:

Résumé: Some novel N-sulfonylphthalimides were synthesized in good yields by condensation of anhydride phthalic with various sulfonamides by two different methods: conventional synthesis and immersion ultrasonic assisted method, in one step. These compounds were screened for their antibacterial activity against Escherichia coli, Staphylococcus aureus, Morganella morganii and Klebsiella pneumoniae.The bioinformatic POM analyses confirm the existence of a antifungal/or antiviral (O d-——O d-) pharmacophore sites. So it will benificial to test these molecules against other biotargets different of bacterial strains such as viruses, fungus and parasites.The molecular structure of 3a was obtained by X-ray diffraction on mono crystal. The crystal packing can be described as alternating layers in zigzag parallel to (100) plane along the c axis, which are connected together with CeH/O hydrogen bonds.

D. Guibedj, H. Bougherara, M. Kadri, H. Akkari, M. Berredjem, A.Khaled. (2019), Methoxyphenyl N-sulfamoyloxazolidinone Cu(II) and Co(II) complexes: Synthesis, DFT/B3LYP (B2PLYP) study and molecular docking. Journal of Molecular Structure

Résumé: nteractions of methoxyphenyl N-sulfamoyloxazolidinone (SOZ) with Cu(II) and Co(II) ions in ethanol at 25 °C were studied experimentally using UV–Vis spectrophotometry. The data processing with a nonlinear least square fitting allowed the determination of stoichiometries, stability constants of the complexes and species distribution diagrams for each complex against ligand concentration. The solid-state complexes were synthesized and characterized by FT-IR,¹ HNMR, thermogravimetric analysis techniques (TGA) and differential scanning calorimetry (DSC) to account for the thermal decomposition of Cu(II) complex. DFT study was performed to obtain insights on SOZ: Cu(II) and/or Co(II) interaction. First, the predicted structural properties of the ligand were compared with the experimental ones obtained from crystallographic data. DFT calculations were performed at B3LYP, B3LYP-D3, B2PLYP and B2PLYP-D3 levels with the same 6–311++G(d,p) basis set and consequently the performance of each exchange functional was tested in the structural properties prediction. Also, global and local chemical reactivity parameters were computed. The most stable metal complexes (1:2) were optimized at B3LYP level in ethanol medium with the CPCM model. Computed FT-IR spectra and TD-DFT results agree with the corresponding experimental data. The interactions were also analyzed and characterized by NBO, MEP and NLO. Finally, a molecular docking was performed to investigate the relative biological activities of the ligand alone and of the metal complexes.

Khadidja Otmane Rachedi, Tan-Sothea Ouk, Rania Bahadi, Abdeslem Bouzina, Seif-Eddine Djouad, Khaoula Bechlem, Rachida Zerrouki, Taibi Ben Hadda, Faisal Almalki, Malika Berredjem.. (2019), Synthesis, DFTandPOManalysesofcytotoxicityactivityof aamidophosphonatesderivatives:Identification ofpotentialantiviral O,O-pharmacophoresite. molecular structure

Résumé: In thepresentstudy,weinvestigatedthecytotoxicactivityofthreecompoundspreparedstartingfrom amino acids.Thesederivativeswereevaluatedfortheir in vitro antitumoractivityagainsthumancell lines (PRI, K562 and JURKAT). Theircytotoxicitywasalsoevaluatedatdifferentconcentrationson severalcelllines.Ontheotherhand,DFTcalculationhasbeenusedtoanalyzetheelectronicandgeo- metriccharacteristics.TheHOMO,LUMOandgapenergieswerealsodeducedforthestablestructurefor each compound.Theseresultswillbecorrelatedwiththeexperimentalvalues.ThebioinformaticPOM (Petra/Osiris/Molinspiration)analysesoftherelativecytotoxicityofthesederivativesarereportedin comparisontoChlorambucil.

(2018), A green, one-pot, three-component and microwave assisted synthesis of α-sulfamidophosphonates. Journal of Materials and Environmental Science.
(2018), A Simple, Efficient, Catalyst-Free and Solvent-Less Microwave-. Journal of the Korean Chemical Society 61 (4)
A. Bouzina, K. Bechlem, H. Berredjem, B. Belhani, I, Becheker, J.Lebreton, Marc Le Borgne, Z. Bouaziz, C, Marminon, Malika Berredjem. (2018), Synthesis, Spectroscopic Characterization, and In Vitro Antibacterial Evaluation of Novel Functionalized Sulfamidocarbonyloxyphosphonates. Molecules

Résumé: Several new sulfamidocarbonyloxyphosphonates were prepared in two steps, namely carbamoylation and sulfamoylation, by using chlorosulfonyl isocyanate (CSI), α-hydroxyphosphonates, and various amino derivatives and related (primary or secondary amines, β-amino esters, and oxazolidin-2-ones). All structures were confirmed by 1H, 13C, and 31P NMR spectroscopy, IR spectroscopy, and mass spectroscopy, as well as elemental analysis. Eight compounds were evaluated for their in vitro antibacterial activity against four reference bacteria including Gram-positive Staphylococcus aureus (ATCC 25923), and Gram-negative Escherichia coli (ATCC 25922), Klebsiella pneumonia (ATCC 700603), Pseudomonas aeruginosa (ATCC 27853), in addition to three clinical strains of each studied bacterial species. Compounds 1a–7a and 1b showed significant antibacterial activity compared to sulfamethoxazole/trimethoprim, the reference drug used in this study.

(2017), Synthesis, X-ray crystallographic and DFT studies of two new N-acylsulfonamides. Journal of Materials and Environmental science
(2017), Ultrasonic assisted green protocol for the synthesis of sulfamides. Phosphorus, Sulfur Silicon and the related elements
(2017), A Novel and Green Method for N-acylation of Amines and Sulfonamides under Ultrasound Irradiation.. Oriental Journal of Chemistry
(2017), A practical and green approach towards synthesis of. Phosphorus, Sulfur, and Silicon and the Related Elements 191 (8), 1086-1091
(2016), Synthesis and antibacterial activity of new chiral N-sulfamoyloxazolidin-2-ones. Journal of Chemical Science
(2016), Efficient synthesis of novel N-acylsulfonamide oxazolidin-2-ones derivatives. Karbala International Journal of Modern Science 2 (2), 98-103

Résumé: A convenient method for the synthesis of new series of N-acylsulfonamide containing oxazolidin-2-one moiety starting from chlorosulfonyl isocyanate and chiral oxazolidinones in two steps (carbamoylation and sulfamoylation), is described. The starting oxazolidinones were obtained in two steps starting from amino acids by reduction with NaBH4 then cyclization in the presence of carbonate diethyl. The synthesis of N-acylsulfonamide oxazolidin-2-ones derivatives has been carried out in excellent isolated yields. The structures of all synthesized compounds were unambiguously confirmed by usual spectroscopic methods 1H NMR, 13C NMR, IR, EA and MS.

(2016), Antihyperglycemic and antidiabetic effects of. European journal of pharmacology 779, 122-130
(2016), Synthesis and antitumor evaluation of novel sulfonylcycloureas . Molecular diversity 20 (2), 399-405
(2016), A Greener, Efficient and Catalyst-Free Ultrasonic-Assisted . Journal of the Brazilian Chemical Society 27 (3), 546-550
Dalila Fedaoui, Abdeslem Bouzina, Yacine Bouhadja, Nour-Eddine Aouf, Malika Berredjem. (2016), Synthesis, Characterization and Spectroscopic Studies of Iron (III) . Der Pharma Chemica
(2016), A New Family of 1,2,3-Oxathiazolidine-2,2-dioxide Phosphonate . phosphorus, sulfur and silicon and the related elements
(2016), The Antibacterial and Cytotoxic Activities of Four New sulfonamide. international journal of pharmaceutical sciences review and research
(2016), Ultrasound assisted green synthesis of α-hydroxyphosphonates . Research on Chemical Intermediates 42, 5993
(2015), A Simple and highly efficient solvent and catalyst-free synthesis of novel N sulfamoyl imines. Green Chemistry Letters and Reviews
(2015), Antidiabetic and Hypolipidemic Potential of 3, 4-dihydroisoquinolin-2(1H)- Sulfonamide in Alloxan In. International Journal of Pharmacology
(2015), One-pot synthesis of novel oxazaphosphinanes under ultrasound irradiation and solvent-free condition. Monatshefte fuer Chemie/Chemical Monthly
(2015), Multicomponent reactions of novel α-sulfamidophosphonates synthesis Under ultrasound irradiation and. RSC Advances
(2015), Greener, Efficient and Catalyst-Free Ultrasonic-Assisted Protocol for the N-Fmoc Protection of Amin. Journal of the Brazilian Chemical Society

Résumé: A simple, eco-sustainable method for the N-(9-fluorenylmethoxycarbonyl) (N-Fmoc) protection of various structurally amines under ultrasonic irradiation is reported. The corresponding N-Fmoc derivatives were obtained in good to excellent yields within short reaction time. The reaction proceeds without the formation of any side product. Mildness, efficiency and easier work are the main advantages of this new protocol.

(2015), Synthesis and spectroscopic study of new substituted phosphoramidates and 1,3,2-diazaphospholidine-. Der Pharma Chemica

Résumé: A new series of substituted 1, 3, 2-diazaphospholidine-2,5-diones was synthesized by an efficient method, starting from a primary amines and amino esters. We have established that phenyl phosphonic dichloride is a suitable reagent allowing the introduction a phosphoryl group. We have prepared the phosphoramidates in two steps. These compounds provide access to 1, 3, 2- diazaphospholidine-2,5-diones by intramolecular cyclization using potassium carbonate.

(2015), Synthesis of Novel Peptidosulfonamides Derived From Modified Oxazolidinones. . research journal of pharmaceutical, biological and chemical sciences

Résumé: The oxazolidin-2-ones are key intermediates in the synthesis of various compounds of interest in terms of reactivity. So, several aminoalcohols were prepared from oxazolidinone. The oxazolidinone may also be used as an intermediate in the preparation of peptidosulfonamide similar sulfonated a natural or synthetic peptide

(2015), Fungitoxic Evaluation of New Modified Amidophosphonates (AP1, AP2) on the in vitro Growth of Two Fun. Research Journal of Environmental Toxicology

Résumé: We performed this work to highlight the in vitro antifungal properties of two amidophosphonates newly synthesized (AP1, AP2). These molecules were synthesized from amino esters and chloroacetyl chloride in two steps using the Michaelis-Arbuzov reaction. We have selected after testing several concentrations 15, 20 and 25 μM for AP1, 10, 25, 40 μM for AP2. The study of the antifungal power by solid medium-diffusion method was performed after microscopic study and purification of fungal isolates from wheat leaves hard, give us the opportunity to identify two fungi: Septoria tritici and Aalternaria tenuis. Results show an antifungal power of two molecules, the growth inhibition-percentage is higher among Aalternaria tenuis. In addition, AP2 molecule appears to have a stronger antifungal activity. Determining the Minimum Inhibitory Concentration (MIC) by the dilution method in liquid medium, shapeless on the effectiveness of our molecules which is to order of 40 μM (AP1) and 25 μM (AP2) for Septoria tritici, 25 μM (AP1) and 15 μM (AP2) for Alternaria tenuis.

(2015), An Eco-friendly and Highly Efficient route for N-acylation under Catalyst-free Conditions . Oriental Journal of Chemistry

Résumé: An eco-friendly, simple, mild, chemo selective and highly efficient procedure for the acylation of primary and secondary amine function in various structurally and electronically aliphatic and aromatic compounds affording their corresponding N-Ac derivatives is developed. Mild conditions, simplicity and easier work-up are the main advantages of this method.

(2015), ChemInform Abstract: A Novel, Rapid and Green Method of Phosphorylation under Ultrasound Irradiatio. RSC Advances

Résumé: The phosphorylation reaction of various N-acylamines, N-acylaminoesters N-acylaminoalcohols and N-acylsulfonamides, with trimethylphosphite or triethylphosphite was effectively promoted under ultrasound irradiation, solvent and catalyst free conditions to produce the corresponding amidophosponate. This rapid method produced the products in short reaction times (5–15 min) and excellent yields (75–90%). This technique at a frequency of 40 kHz, strongly accelerate the process of formation P-C bond compared to the classic Arbuzov reaction.

(2014), Synthesis and antibacterial activity of sulfonamides. SAR and DFT studies. Journal of Molecular Structure : Elsevier,
(2014), Cytotoxic study of three derivatives Amidophosphonates on alternative cellular model: Paramecium te. Toxicology research : RSC,
(2014), Convenient synthesis of novel N-acylsulfonamides containing phosphonate moiety . Phosphorus, Sulfur and Silicon and related elements : Taylor and Francis,
(2014), A Simple and Eco-Sustainable Method for the Sulfonylation of Amines Under Microwave-Assisted Solven. RSC advances : RSC,
(2014), Efficient synthesis, characterization and antibacterial activity of novel N-acylsulfonamides and su. Phosphorus, sulfur and silicon and related elements : Taylor and Francis,
(2014), An efficient method for the synthesis of novel Nacylsulfonamides using Tin (IV) chloride as cata. phosphrus, sulfur and silicon and related elements : Taylor and Francis,
(2014), A simple, rapid, and efficient N-Boc protection of amines under ultrasound irradiation and catalyst-. Monatshefte fur Chemie : Springer,
(2014), Synthesis of a new series of sulfonamides containing isatin moiety . PhytoChem & BioSub Journal.
(2014), Microwave-assisted a new, efficient, and catalyst-free approach for formation of O-tert-butoxy carbo. Chemistry Letters 03/2014
(2014), Induction of oxidative stress in Paramecium aurelia exposed to a novel phosphoramidate . Fresenius Environmental Bulletin
(2014), An efficient method for the synthesis of novel N-sulfonylimines using TBAB under solvent-free condi. journal of chemical and pharmaceutical research

Résumé: The condensation of various sulfonamides with aromatic aldehydes was effectively promoted in the presence of TBAB to produce the corresponding sulfonylimine products in good yields under solvent-free conditions. The sulfonamides were prepared starting from chlorosulfonylisocyanate (CSI), primary amine in three steps (carbamoylation, sulfamoylation and deprotection). An efficient method for the synthesis of novel N-sulfonylimines using TBAB under solvent-free conditions. Available from: [accessed May 14, 2015].

(2014), Antibacterial activity of four sulfonamide derivatives against multidrug-resistant Staphylococcus au. Journal of chemical and pharmaceutical research

Résumé: This study aims to evaluate, in vitro, antibacterial activity of four novel sulfonamide derivatives (1a-d) against Staphylococcus aureus: reference strain ATCC 25923 and 40 clinical isolates. Inhibition zones were performed with the disk diffusion method. The MIC values were determined by the dilution broth method. A 48 hours MIC-Kinetic curve was performed for the tested compounds. All compounds showed significant antibacterial activity. The mean values of the inhibition zones diameter for compounds 1a-d were 22.15 ± 6.22, 16.39 ± 1.17, 15.42 ± 0.66 and 15.83± 1.28 mm, respectively (p value = 0.001). The MIC values were ranged between 64 and 512 g/ml. The compound 1b showed better activity. The 48 hours MIC-kinetic curve showed an inhibiting bacterial growth. The studied compounds 1a-d showed a promising antibacterial effect to response to the urgent need for innovative drugs that could be more effective against resistant pathogens. Antibacterial activity of four sulfonamide derivatives against multidrug-resistant Staphylococcus aureus. Available from: [accessed May 14, 2015].

(2014), In-vitro Antibacterial Activity of two Novel Sulfonamide Derivatives against Urinary Strains of Esch. Research Journal of Pharmaceutical, Biological and Chemical Sciences

Résumé: Two novel sulfonamide derivatives, the 3,4-dihydroisoquinoline-2(1H)-sulfonamide (1a) and the 4phenylpeperazine sulphonamide (1b), have been evaluated in vitro as antibacterial agents against urinary and standard strains of Gram-negative Escherichia coli, by both disk diffusion and dilution assay methods. These bacteria were screened against the novel compounds which were compared to a standard antibiotic, the sulfamethoxazol-trimethoprim (STX). The results revealed that the tested compounds showed a good antibacterial activity. The diameters of the growth inhibition area were in the range 10-40 mm. Antibacterial activity of compound 1a, against all the bacterial strains, was superior to those of the compound 1b and the commercial drug SXT. The diameters of the growth inhibition area of sulfonamide 1a were in the range 15-40 mm and the MICs were ranged from 2 to 128 g/ml. Compound 1b was less active than compound 1a but more active than antibiotic SXT. Diameters of inhibition of compound 1b were in the range 4-26 mm and the MICs were ranged from 8 to 256 µg/ml. In conclusion, the newly synthesized sulfonamide derivatives showed a powerful interesting antibacterial activity against all strains of Escherichia coli. Better activity was obtained with compound 1a. In-vitro Antibacterial Activity of two Novel Sulfonamide Derivatives against Urinary Strains of Escherichia coli.. Available from: [accessed May 14, 2015].

(2013), Synthesis and structural study of N-acetyl-1,2,3,4-tetrahydroisoquinoline- 2-sulfonamide obtained. Journal of molecular Structure : Elsevier,
(2013), Host-guest interaction between 3,4-dihydroisoquinoline-2(1H)-sulfonamide and β-cyclodextrin: Spe. Journal of molecular structure
(2013), Synthesis and antibacterial activity of novel N-acylsulfonamides. Arabian journal of chemistry : Elsevier,
(2013), Efficient synthesis and antibacterial activity of novel cyclic sulfamides . Rasayan journal of chemistry : Elsevier,
(2013), Synthesis and biological activity of new chiral N-acylsulfonamide bis-oxazolidin-2-ones. Journal of . Journal of Heterocyclic chemistry
(2013), Efficient synthesis of modified sulfamides and cyclosulfamides containing phosphonate moieties . Phosphorus, Sulfur and Silicon and the Related Elements : Taylor and Francis,
(2013), A simple and eco-sustainable method for the O-Boc protection/deprotection of various phenolic struct. Green Chemistry Letters and Reviews 6 (3) , pp. 211
(2012), Synthesis and structural study of new substituted chiral sulfamoyl oxazolidin-2-ones . Tetrahedron : Elsevier,
(2012), Efficient deprotection of Boc Group in sulfamides using heteropolyacid catalyst (HPA).. European journal of chemistry
(2012), Toxic effects of phosphoramidate on Paramecium sp. with special emphasis on respiratory metabolism, . Toxicological and Environmental Chemistry : Taylor and Francis,
(2012), Effect of novel phosphoramidate on growth and respiratory metabolism of Paramecium aurelia . Journal of Natural Science, Biology and Medicine
(2012), Efficient method for the synthesis of α-amidophosphonates via the michaelis-arbuzov reaction. Phosphrus, sulfur and silicon and related elements : Taylor and Francis,
(2012), Synthesis of oxazolidin-2-ones phosphonates derivatives: Toxic effect on paramecium species. Rasayan Journal of Chemistry 5 (4) , pp. 450
(2012), A Simple and Efficient Green Method for the Deprotection of N-Boc in Various Structurally Diverse A. International Journal of Chemistry. 01/2012; 4
(2012), Efficient Method for the Synthesis of Diazaphospholidines: Toxicological Evaluation . American Journal of Organic Chemistry
(2012), N-tert-Butoxycarbonylation of Structurally Diverse Amines and Sulfamides under Water-Mediated Catal. ISRN organic chemistry. 01/2012; 2012:404235.
(2011), Synthesis and biological activity of new chiral N-acylsulfonamides bis –oxazolidin-2-ones . Journal of Chemistry and Chemical Engineering. 01/2011; 5.
(2010), (4S)-4-Benzyl-N-{[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]sulfonyl} -2-oxo-1,3-oxazolidine-3-carboxa. Acta Crystallographica Section E: Structure Reports Online
(2010), Crystal structure of 4-phenyl-piperazine-1-sulfonamide. X-ray Structure Analysis Online 26 (3) , pp. 13
(2008), A new sulfa-heterocyclic compounds containing aziridine moiety, 3-benzyl-2-thia-1,3-diazabicyclo[3.1. Heterocycles 75 (9) , pp. 2243
(2008), 1,2,3,4-Tetrahydroisoquinoline-2-sulfonamide. Acta Crystallographica Section E: Structure Reports Online 64 (2)
(2007), New pseudonucleosides containing chiral oxazolidin-2-ones and Cyclosulfamides as aglycones: Synthesi. Nucleosides, Nucleotides and Nucleic Acids 26 (10-12) , pp. 1539
(2006), Efficient synthesis of chiral 1,1′-sulfonyl bisaziridines. Synthetic Communications 36 (16) , pp. 2299
(2006), Cyclosulfamides as constraint dipeptides: The synthesis and structure of chiral substituted 1,2,5-th. Phosphorus, Sulfur and Silicon and the Related Elements 181 (6) , pp. 1351
(2006), Simple and efficient synthesis of new chiral N,N′-sulfonyl Bis-oxazolidin-2-ones. Heteroatom Chemistry 17 (1) , pp. 61
(2004), N-chlorosulfonyloxazolidin-2-ones: Synthesis, structure, and reactivity toward aminoesters. Synthetic Communications 34 (9) , pp. 1653
(2004), Simple and Efficient Cleavage Reaction of the Boc Group in Heterocyclic Compounds. Journal of Heterocyclic Chemistry 41 (1) , pp. 57
(2003), Synthesis of new pseudonucleosides containing chiral cyclosulfamides as agycone. Nucleosides, Nucleotides and Nucleic Acids 22 (5-8) , pp. 671
(2003), Regiospecific synthesis and N-acylation of chiral 1,2,5-thiadiazolidines 1,1-dioxides | Synthese e. Phosphorus, Sulfur and Silicon and the Related Elements 178 (4) , pp. 693
(2000), Synthèse et cyclisationde carboxylsulfamides dérivés d'amines et d'α-hydroxyesters. Évaluation de l'. Phosphorus, Sulfur and Silicon and Related Elements 165 , pp. 249