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

doi:10.3390/molecules23071682

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

Molecules. 2018 Jul 10;23(7):1682. doi: 10.3390/molecules23071682.

Authors

Affiliations

¹ Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Badji-Mokhtar-Annaba University, Box 12, 23000 Annaba, Algeria. [email protected].
² Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Badji-Mokhtar-Annaba University, Box 12, 23000 Annaba, Algeria. [email protected].
³ Laboratory of Applied Biochemistry and Microbiology, Department of Biochemistry, Badji-Mokhtar-Annaba University, Box 12, 23000 Annaba, Algeria. [email protected].
⁴ Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Badji-Mokhtar-Annaba University, Box 12, 23000 Annaba, Algeria. [email protected].
⁵ Laboratory of Applied Biochemistry and Microbiology, Department of Biochemistry, Badji-Mokhtar-Annaba University, Box 12, 23000 Annaba, Algeria. [email protected].
⁶ 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. [email protected].
⁷ 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. [email protected].
⁸ 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. [email protected].
⁹ 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. [email protected].
¹⁰ Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Badji-Mokhtar-Annaba University, Box 12, 23000 Annaba, Algeria. [email protected].

Abstract

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.

Keywords: antibacterial activity; carbamoylation; phosphonates; sulfamides; sulfamoylation.

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Bacteria / drug effects
Humans
Microbial Sensitivity Tests
Organophosphonates / chemical synthesis*
Organophosphonates / chemistry
Organophosphonates / pharmacology*
Oxazoles / chemical synthesis
Oxazoles / chemistry
Oxazoles / pharmacology
Pharmaceutical Preparations / chemistry

Substances

Anti-Bacterial Agents
Organophosphonates
Oxazoles
Pharmaceutical Preparations
oxazolidine