1,2,3,4-Tetra­hydro­isoquinoline-2-sulfonamide

The title compound, C9H12N2O2S, is a useful precursor of a variety of modified sulfonamide mol­ecules. Due to the importance of these mol­ecules in biological systems (antibacterials, antidepressants and many other applications), there is a growing inter­est in the discovery of new biologically active compounds. In the title compound, the mol­ecules are linked by N—H⋯O inter­molecular hydrogen bonds involving the sulfonamide function to form an infinite two-dimensional network parallel to the (001) plane

Efficient deprotection of Boc group in amines and sulfamides using Dawson heteropolyacid catalyst

A series of sulfamides containing two protecting groups have been synthesized starting from N-benzoylaminoacids derivatives of (glycine, alanine, valine, leucine, phenylalanine), chlorosulfonylisocyanate and primary amines. Selective deprotection of the cyclic or linear sulfamides and amines has been achieved by treatment with heteropolyacid, which is easily recoverable and reusable. This method represents a reasonable alternative to the previous reported deprotection procedures

(4S)-4-Benzyl-N-{[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]sulfon­yl}-2-oxo-1,3-oxazolidine-3-carboxamide

The title compound, C21H21N3O7S, contains an oxazolidinone ring and a sulfonamide group, both characteristic for biologically and pharrmaceutically active compounds. Both stereogenic centres reveal an S absolute configuration. The two oxazolidinone rings are in an envelope conformation with the methyl­ene carbon flap atoms deviating by 0.428 (1) and 0.364 (2) Å from the best least-square planes formed by the four other ring atoms. An intra­molecular N—H⋯O hydrogen bond contributes to the folded conformation of the mol­ecule. In the crystal, weak inter­molecular C—H⋯O inter­actions connect the mol­ecules into helices along the the twofold screw axes

Quantum computational calculations of novel N-sulfonylimine derivatives

A computer model based on the density functional theory (DFT) was developed for the identification of the physico-chemical parameters governing the bioactivity of novel N-sulfonylimine derivatives 1a-1f containing a potential antibacterial pharmacophore sulfonamide unit. This study was performed using DFT / B3LYP with 6-31G (d, p) basis set. Information on the size, shape, charge density distribution, and site of chemical reactivity of molecules 1a-1f was obtained by mapping the electron density isosurface with the electrostatic potential surface. The energies of frontier molecular orbitals and the LUMO-HOMO energy gap are measured to explain electronic transitions. To find the most reactive sites of the molecules studied, condensed Fukui functions were also calculated. The six compounds 1a-1f analyzed here were previously synthesized by our group. Un modèle informatique basé sur la théorie fonctionnelle de la densité (DFT) a été développé pour l'identification des paramètres physico-chimiques régissant la bioactivité de nouveaux dérivés de N-sulfonylimine 1a-1f contenant une pharmacophore antibacterien potential sulfonamide.  Cette étude a été réalisée en utilisant la méthode DFT / B3LYP avec la base 6-31G (d, p). Des informations sur la taille, la forme, la distribution de densité de charge et le site de réactivité chimique des molécules 1a-1f ont été obtenues en cartographiant l'isosurface de densité électronique avec la surface de potentiel électrostatique. Les énergies des orbitales moléculaires frontières et l'écart énergétique LUMO-HOMO sont mesurés pour expliquer les transitions électroniques. Pour trouver les sites les plus réactifs des molécules étudiées, des fonctions de Fukui condensées ont également été calculées. Les six composés 1a-1f que nous avonts analysés ont été préalablement synthétisés par notre groupe

A convenient synthesis, in silico study and crystal structure of novel sulfamidophosphonates: Interaction with SARS-CoV-2

International audienceA one-pot synthetic strategy was developed for the synthesis of novel sulfamidophosphonates via a threecomponent Kabachnik-Fields reaction of sulfanilamide, triethyl phosphite, and various aldehyde using ultrasound irradiation. Seven organophosphorus derivatives were synthesized with high yields through this newly developed method. The target compounds were characterized by 1 H, 31 P, 13 C NMR, and IR. The molecular structure of 4a was obtained by X-ray diffraction on the monocrystal. Crystal belongs to the orthorhombic system with space groups Pbca. Insight into the binding mode of the synthesized compounds (ligand) into the binding sites of SARS-CoV2 (PDF code: 5R80) was provided by docking studies, performed with the help of Maestro 9.0 docking software

Simple and efficient synthesis of new chiral N,N'-sulfonylbis[2-oxazolidinones]

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Synthesis and antibacterial activity of novel N-acylsulfonamides

A series of novel N-acylsulfonamide derivatives were synthesized and characterized by 1H NMR, 13C NMR and HRMS. The N-acylsulfonamides were prepared in four steps (carbamoylation, sulfamoylation, deprotection and acylation) starting from chlorosulfonyl isocyanate. These compounds were evaluated in vitro as antimicrobial agents against representative strains of Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli, Acinetobacter, Klebsiella pneumonia and Pseudomonas aeruginosa)

A one-pot three-component synthesis of novel α-sulfamidophosphonates under ultrasound irradiation and catalyst-free conditions

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Synthesis, Spectroscopic Characterization, and In Vitro Antibacterial Evaluation of Novel Functionalized Sulfamidocarbonyloxyphosphonates

International audienceSeveral 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 1 H, 13 C, and 31 P 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