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

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

Valorisation d une plante médicinale algérienne paronychia argentea et essai de couplage et évaluation des propriétés antitumorales d hétérocycles azotes polyphosphorylés

Cette étude vise à valoriser une plante médicinale de la flore locale Paronychia argentea utilisée dans la médecine traditionnelle algérienne comme antilithiasique. Dans un premier temps, deux extraits aqueux et butanolique de cette plante ont été étudiés. Les effets pharmacologiques de la plante indiquent que l'administration de l'extrait butanolique des parties aériennes de Paronychia argentea aux rats rendus lithiasiques par une injection intrapéritonéale de l oxalate de sodium, réduit et empêche la croissance des calculs urinaires, soutenant les données et les croyances traditionnelles concernant l'activité antiurolithiasique de la plante. Le mécanisme sous-tendant cet effet et les substances actives qui différencient les deux extraits sont toujours inconnus. Probablement, cet effet antilithiasique est peut être lié à l'abaissement des concentrations urinaires des constituants formant les calculs et/ou l'activité antioxydante de principe(s) actif(s) dans l'extrait qui permet(tent) l élimination des radicaux libres. L étude de la toxicité aiguë et subaiguë des extraits de Paronychia argentea, par voie orale sur des rats normaux, n'a pas induit de changements ou altérations significatives des paramètres biochimiques, hématologiques et morphologiques chez ces rats aux doses expérimentées. Dans un deuxième temps, la synthèse d hétérocycles azotés (chlorosulfonyl oxazolidinones) a été réalisée avec succès. Le couplage de ces molécules au BPA3 (néridronate), afin d'améliorer leur biodisponibilité et leur activité antitumorale pour les comparer à l extrait butanolique de Paronychia argentea, n a malheureusement pas donné les résultats escomptés.This study aimed at develop a medicinal plant of the local flora Paronychia argentea used in Algerian traditional medicine like antilithiasic. In the first part of this work, aqueous and butanolic extracts of this plant were carried out. The pharmacological effects of the plant indicated that administration of the butanolic extract of PA aerial parts to rats with experimental nephrolithiasis, reduced and prevented the growth of urinary stones, supporting folk information regarding antiurolithiasic activity of the plant. The mechanism underlying this effect and the active ingredients, which differentiate the two extracts, is still unknown. Apparently, it could be related to lowering of urinary concentrations of stone forming constituents, antioxidant activity and free radical scavenging principle(s) contained in the extract. The acute and sub acute oral administration of Paronychia argentea extracts did not induce significant alterations in almost all biochemical, haematological and morphological parameters in these rats. In the second time, the synthesis of the containing-nitrogen heterocycles (chlorosulfonyl oxazolidinones), was carried out successfully. Coupling of these molecules to the BPA3 (neridronate), in order to improve their biodisponibility and their antitumor activity to compare them with the extract butanolic of Paronychia argentea, did not give the anticipated results.PARIS13-BU Sciences (930792102) / SudocSudocFranceF

A New Class of Heterocycles: 1,4,3,5-Oxathiadiazepane 4,4-dioxides

This work reports the synthesis of novel 1,4,3,5-oxathiadiazepanes 4,4-dioxides from the reaction of N’-benzyl-N-(2-hydroxyethyl)-sarcosine or proline sulfamide with aromatic aldehydes under acid catalysis. To prepare the starting materials N-Boc-sulfamide derivatives of sarcosine or proline were alkylated with benzyl alcohol under Mitsunobu reaction conditions, the Boc group was removed chemoselectively by acidolysis, and the resulting product reduced to the corresponding alcohol in good yields

Selected Chemical and Spectral Proprieties and Antimicrobial Evaluation †

Abstract: The sulfamide functional group is increasingly relevant in both medicinal and bioorganic chemistry. We report here practical access to a series of N2,N5-substituted five-membered cyclosulfamides. The five-membered heterocyclic motif was prepared starting from proteogenic amino acids and chlorosulfonyl isocyanate via the Mitsunobu reaction. Selected chemical and spectral proprieties and the antimicrobial evaluation of these compounds are detailed

A New family of Sulfamidophosphonates Derivatives: Microwave‐Accelerated Multicomponent Synthesis, Characterization and X‐Ray Crystallographic Study**

In this present study, we describe a simple, effective and greener one-pot microwave-assisted synthesis of novel αsulfamidophosphonates 4 (a-l), and 5 (a,b) that were rationally designed and synthesized following the principle of the superposition of bioactive substructures. This reaction was accomplished by the condensation of various aromatic aldehydes, sulfamide and diethyl phosphite via the Kabachnik-Field

New efficient synthesis, spectroscopic characterization, and X-ray analysis of novel β-enaminocarboxamide derivatives

International audienceA new series of β-enaminocarboxamide was synthesized via the addition of chlorosulfonyl isocyanate to β-enaminones. The prepared intermediates were converted to corresponding β-enaminocarboxamides by removal of the chlorosulfonyl group using methanol. The resulting compounds were obtained in excellent yields in the range of (80-92%) and were characterized by 1 H, 13 C, HMBC, HSQC NMR spectroscopy, and IR spectroscopy as well as elemental analysis. 1 H-NMR spectrum showed a non-equivalence of the primary amide protons which was due to H-bonding. β-enaminocarboxamide 5h was obtained as a crystal and was subjected to X-ray analysis. Results showed that 5h crystallizes in the monoclinic crystal system with C2/c space group and the ORTEP confirmed the presence of intramolecular H-bonds