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

• Published in: Molecules (Basel, Switzerland) Vol. 23; no. 7; p. 1682
• Main Authors: Bouzina, Abdeslem, Bechlem, Khaoula, Berredjem, Hajira, Belhani, Billel, Becheker, Imène, Lebreton, Jacques, Le Borgne, Marc, Bouaziz, Zouhair, Marminon, Christelle, Berredjem, Malika
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 10.07.2018; MDPI
• Subjects: Amines; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Bacteria - drug effects; Bacteriology; carbamoylation; Chemical Sciences; Esters; Humans; Infrared spectroscopy; Isocyanates; Klebsiella; Life Sciences; Magnetic resonance spectroscopy; Mass spectroscopy; Medication; Medicinal Chemistry; Microbial Sensitivity Tests; Microbiology and Parasitology; NMR spectroscopy; Organic chemistry; Organophosphonates - chemical synthesis; Organophosphonates - chemistry; Organophosphonates - pharmacology; Oxazoles - chemical synthesis; Oxazoles - chemistry; Oxazoles - pharmacology; Pharmaceutical Preparations - chemistry; Pharmaceutical sciences; Pharmacology; phosphonates; Pseudomonas aeruginosa; Spectroscopy; Spectrum analysis; Sulfamethoxazole; sulfamides; sulfamoylation; Trimethoprim; antibacterial activity; sulfamoylation; carbamoylation; phosphonates; sulfamides
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules23071682

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, C, and P NMR spectroscopy, IR spectroscopy, and mass spectroscopy, as well as elemental analysis. Eight compounds were evaluated for their antibacterial activity against four reference bacteria including Gram-positive (ATCC 25923), and Gram-negative (ATCC 25922), (ATCC 700603), (ATCC 27853), in addition to three clinical strains of each studied bacterial species. Compounds ⁻ and showed significant antibacterial activity compared to sulfamethoxazole/trimethoprim, the reference drug used in this study.