Synthesis, Spectroscopic Characterization, and In Vitro Antibacterial Evaluation of Novel Functionalized Sulfamidocarbonyloxyphosphonates
Abdeslem Bouzina,
Khaoula Bechlem,
Hajira Berredjem,
Billel Belhani,
Imène Becheker,
Jacques Lebreton,
Marc Le Borgne,
Zouhair Bouaziz,
Christelle Marminon,
Malika Berredjem
Affiliations
Abdeslem Bouzina
Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Badji-Mokhtar—Annaba University, Box 12, 23000 Annaba, Algeria
Khaoula Bechlem
Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Badji-Mokhtar—Annaba University, Box 12, 23000 Annaba, Algeria
Hajira Berredjem
Laboratory of Applied Biochemistry and Microbiology, Department of Biochemistry, Badji-Mokhtar-Annaba University, Box 12, 23000 Annaba, Algeria
Billel Belhani
Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Badji-Mokhtar—Annaba University, Box 12, 23000 Annaba, Algeria
Imène Becheker
Laboratory of Applied Biochemistry and Microbiology, Department of Biochemistry, Badji-Mokhtar-Annaba University, Box 12, 23000 Annaba, Algeria
Jacques Lebreton
CNRS, Université de Nantes, Chimie et Interdisciplinarité: Synthèse, Analyse, Modélisation (CEISAM), UMR CNRS 6230, 2 rue de la Houssinière, BP92208, CEDEX 3, 44322 Nantes, France
Marc Le Borgne
Université de Lyon, Université Lyon 1, Faculté de Pharmacie—ISPB, EA 4446 Bioactive Molecules and Medicinal Chemistry, SFR Santé Lyon-Est CNRS UMS3453—INSERM US7, CEDEX 8, 69373 Lyon, France
Zouhair Bouaziz
Université de Lyon, Université Lyon 1, Faculté de Pharmacie—ISPB, EA 4446 Bioactive Molecules and Medicinal Chemistry, SFR Santé Lyon-Est CNRS UMS3453—INSERM US7, CEDEX 8, 69373 Lyon, France
Christelle Marminon
Université de Lyon, Université Lyon 1, Faculté de Pharmacie—ISPB, EA 4446 Bioactive Molecules and Medicinal Chemistry, SFR Santé Lyon-Est CNRS UMS3453—INSERM US7, CEDEX 8, 69373 Lyon, France
Malika Berredjem
Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Badji-Mokhtar—Annaba University, Box 12, 23000 Annaba, Algeria
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.
