Next Article in Journal
Antimicrobial Peptides: Powerful Biorecognition Elements to Detect Bacteria in Biosensing Technologies
Next Article in Special Issue
Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds
Previous Article in Journal
Comparative Strengths of Tetrel, Pnicogen, Chalcogen, and Halogen Bonds and Contributing Factors
Previous Article in Special Issue
Correction: El-kalyoubi, S.; et al. Novel 2-Thioxanthine and Dipyrimidopyridine Derivatives: Synthesis and Antimicrobial Activity. Molecules, 2015, 20, 19263–19276
Article Menu
Issue 7 (July) cover image

Export Article

Open AccessArticle
Molecules 2018, 23(7), 1682; https://doi.org/10.3390/molecules23071682

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

1
Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Badji-Mokhtar—Annaba University, Box 12, 23000 Annaba, Algeria
2
Laboratory of Applied Biochemistry and Microbiology, Department of Biochemistry, Badji-Mokhtar-Annaba University, Box 12, 23000 Annaba, Algeria
3
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
4
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
*
Authors to whom correspondence should be addressed.
Received: 18 June 2018 / Revised: 4 July 2018 / Accepted: 5 July 2018 / Published: 10 July 2018
(This article belongs to the Collection Heterocyclic Compounds)
Full-Text   |   PDF [5283 KB, uploaded 10 July 2018]   |  

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 1a7a and 1b showed significant antibacterial activity compared to sulfamethoxazole/trimethoprim, the reference drug used in this study. View Full-Text
Keywords: sulfamides; phosphonates; carbamoylation; sulfamoylation; antibacterial activity sulfamides; phosphonates; carbamoylation; sulfamoylation; antibacterial activity
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Bouzina, A.; Bechlem, K.; Berredjem, H.; Belhani, B.; Becheker, I.; Lebreton, J.; Le Borgne, M.; Bouaziz, Z.; Marminon, C.; Berredjem, M. Synthesis, Spectroscopic Characterization, and In Vitro Antibacterial Evaluation of Novel Functionalized Sulfamidocarbonyloxyphosphonates. Molecules 2018, 23, 1682.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top