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.
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.
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.
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.
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.
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.
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.
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.
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
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.
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.
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.
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: https://www.researchgate.net/publication/268186036_An_efficient_method_for_the_synthesis_of_novel_N-sulfonylimines_using_TBAB_under_solvent-free_conditions [accessed May 14, 2015].
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: https://www.researchgate.net/publication/270760765_Antibacterial_activity_of_four_sulfonamide_derivatives_against_multidrug-resistant_Staphylococcus_aureus [accessed May 14, 2015].
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: https://www.researchgate.net/publication/271133815_In-vitro_Antibacterial_Activity_of_two_Novel_Sulfonamide_Derivatives_against_Urinary_Strains_of_Escherichia_coli [accessed May 14, 2015].