Publications internationales
Résumé: A sonochemistry-based method was used to synthesize a novel series of N-cyclic imides substituted benzenesulfonamide using montmorillonite K10 as an efficient catalyst. Yields and reaction times needed for reaction completion using conventional heating, microwave (MW) and ultrasound (US) irradiation are compared. The environmentally friendly sonochemical method, in the presence of electron withdrawing and electron donating groups, afford the desired products in high yields and short time. The structures of the products were characterized by spectral data (1H, 13C NMR, and mass spectrometry). Molecular docking study was performed in order to evaluate synthesized compounds as possible inhibitors of human carbonic anhydrase I and II and their interactions in binding sites. Moreover, absorption, distribution, metabolism, and excretion properties were also assessed via Molinspiration software and all compounds obeyed Lipinski's rule of five. In conclusion, the overall results of our study reveal that the synthesized compounds could be potential candidates in the search for novel carbonic anhydrases inhibitors.
Résumé: Some new aryl sulfones containing a cyclic imide moiety were synthesized using a cesium salt of Dawson-type tungstophosphoric acid (Cs5HP2W18O62) as an efficient catalyst under ultrasound irradiation. This efficient method affords the desired products in one step with high chemical yields. All structures of the products were proven by mass spectrometry and 1H and 13C NMR spectroscopy. The submission of the molecules to the Molinspiration software showed that they fulfill Lipinski’s rule of five. Moreover, molecular docking studies performed on the compounds against Staphylococcus aureus tyrosyl-tRNA synthetase and Candida albicans dihydrofolate reductase revealed the potential binding mode of the ligands to the sites of the appropriate targets. Some compounds were evaluated in vitro as antimicrobial agents against 16 strains. The results indicate that the tested molecules show a good activity at low concentrations (minimum inhibitory concentration ¼ 0.125 mg/mL) against selected microbial strains.
Résumé: An efficient and convenient protocol for the one-pot synthesis of new benzothiazoles bearing sulfonamide or cyclic imide moieties using Cesium salt of Wells–Dawson heteropolyacid (Cs5HP2W18O62) as solid catalyst and water as solvent under ultrasound irradiation was reported. The reaction speed was remarkably catalyzed with the aid of ultrasound irradiation. Moreover, this approach prepares multiple other benefits such as operational ease, higher yields and energy performance.
Résumé: A simple and efficient preparation of novel series of mono‐ and bis‐pyrrolidine‐ 2,5‐diones containing sulfonamide moiety was described. The strategy involved sequential one‐pot sulfonylation‐nucleophilic substitution procedure and was found effective under ultrasound activation and used for the first time. This approach allows the synthesis of products in good to excellent yields in short reaction time.
Résumé: N-acylation of substituted sulfonamides with different anhydrides in the presence of Cesium salt of Wells–Dawson heteropolyacid (Cs 5 HP 2 W 18 O 62 ) as an efficient and reusable catalyst was investigated for the first time. Cs 5 HP 2 W 18 O 62 was used with a catalytic amount in water as a green solvent. At room temperature, a series of N-acylsulfonamides were synthesized, while under refluxing conditions, new cyclic imides containing sulfonyl group were obtained. Atom-economy, high yields, easy work-up, as well as simple catalyst recovery and reusabil- ity are the key features of this procedure.
Résumé: In this study, the photocatalytic degradation of seven sulfur compounds (2-methylthiophene, 3-methylthiophene, 2-phenylthiophene, 3-phenylthiophene, 2,5-diphenylthiophene, 2-(2-thienyl) pyridine, and 2- (3-thienyl) pyridine in semiaqueous medium are compared to thiophene. The apparent-reaction-rate constant (k) is found to decrease in the following order: 2,5-diphenylthiophene > 2-(2-thienyl) pyridine > 2- penhylthiophene > 3-penhylthiophene > 2-(3-thienyl) pyridine > 3- methylthiophene > 2-methylthiophene > thiophene. From the data obtained by UV light absorption (λ max ) measurements and electronic structure calculations (frontier orbitals energy, global hardness, and global softness), the kinetic parameters of the reaction have been determined. Among the studied compounds, thiophene with a high λ max and low calculated LUMO−HOMO gap energy has showed higher activity under UV irradiation. Interestingly, a lower activity is observed with low λ max and high LUMO−HOMO gap energy. This demonstrates, for the first time, that the reactivity depends essentially on the thermodynamic stability of the sulfur compound rather than on the nature or the position of the substituent on the ring.
Résumé: H 6 P 2 W 18 O 62 is used as an efficient catalyst for the synthesis of novel N- substituted sulfonyl maleimides (1H-Pyrrole-2,5-diones) via the condensation of sulfonamide and maleic anhydride derivatives. The Dawson heteropolyacid was used with a catalytic amount of 2 mmol % in acetonitrile at reflux. The reuse of H 6 P 2 W 18 O 62 as heterogeneous catalyst several times without decrease their activity, short reaction times,easy isolation of desired products with good to excellent yields shows the advantages of this novel methodology.
Résumé: The synthesis of new series of pyrrolidine-2,5-diones having sulfonamide moieties is described. These compounds are synthesized in good yield in three steps (carbamoylation- sulfamoylation, deprotection and condensation) using a catalytic amount of H 6 P 2 W 18 O 62 in acetonitrile under refluxing conditions.
Résumé: At room temperature and under acidic conditions, acylation of sulfamides derivatives in various solvents using diverse solid catalysts has been investigated. The best yields are obtained in acetonitrile with a Wells-Dawson type heteropolyacid H 6 P 2 W 18 O 62 as acidic solid catalyst. Crystals of N-acetyl-1,2,3,4-tetrahydroisoquinoline-2-sulfonamide suitable for X-ray study have been obtained after recrystallization in toluene. The detailed analysis of molecular and crystal structure is presented in comparison with the structure of 1,2,3,4- tetrahydroisoquinoline-2-sulfonamide, before acylation, previously studied by our team. The role of both intra- and intermolecular weak interactions is discussed. The Hirshfeld surfaces analysis in form of d norm representation and decomposed fingerprint plots were used to find out different weak but directional hydrogen bonds and π interactions. Both structures present similar sandwich structures with alternation of primary layers involving strong hydrogen bonds with secondary layers involving mostly weaker interactions.
Résumé: The photocatalytic degradation of some benzene derivatives over TiO(2) (Phenol, Chlorobenzene and Toluene) in aqueous medium is compared to the reaction of the benzene. The rates of disappearence fit Langmuir-Hinshelwood kinetics and the parameter k has been determined. The electronic effect of the substituent is responsible of the kinetic of photodegradation of the aromatic compound and can lead to particular modes of adsorption on catalyst: more reactivity is observed with an electron-donating substituent. New concepts for new photocatalysts can then be defined by doping foreign materials into TiO(2) photocatalyst.