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

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.

Antibacterial, Cytotoxic and Genotoxic Assessment of New Sulfonamide Derivatives

“…[29] Bouzina and al. [30] evaluated the antibacterial activity of a new series of sulfamidocarbonyloxyphosphonates and demonstrated that all tested compounds had an important inhibition against Gram negative strains than Gram positive. This finding supports our findings, showing that sulfonamide chemicals are more efficient against Gram negative bacteria.…”

Cyclic N‐2‐Chloroethyl‐sulfamide Compounds with a Phosphonate Moiety: Synthesis, Characterization, X‐Ray Crystallographic Study and Antimicrobial Evaluation

“…In this work, a series of seven N,N-bis (2-chloroethyl) sulfamido carbonyloxymethylphosphonate derivatives (1 b-7 b) and their cyclic analogs (1 c-7 c) were synthesized by a carbamoylationsulfamoylation reaction of seven α-hydroxyphosphonates, followed by intramolecular cyclization. The impact of the aromatic substituent in the alpha position of the phosphonate Compound 5 [25] Treatment…”

“…Because sulfonamide and sulfamide compounds have been widely studied for their antimicrobial activities some sulfonamidocarbonyloxymethylphosphonates were also recently developed in our laboratory, as potential antimicrobial agents against Gram-positive and negative bacteria and have shown significant antibacterial activity [25] compared to sulfamethoxazole/trimethoprim as a reference (Figure 1, compound 5).…”

Novel pseudonucleosides and sulfamoyl-oxazolidinone β - D -glucosamine derivative as anti-COVID-19: design, synthesis, and in silico study

“…Furthermore, the introduction of cyclosulfamide and Nsulfamoyloxazolidin-2-one into glucosamine structure can lead to interesting new chemical and pharmacological potentialities due to their biological activities with a broad application as synthetic intermediates (Bouzina et al, 2021;Nicolaou et al, 2004) especially in the asymmetric synthesis (F ecourt et al, 2010). They present a variety of interesting and useful properties that make them attractive as cyclic scaffolds for peptidomimetics in the design of protease inhibitors such as HIV protease (Hult en et al, 1999;Jadhav & Woerner, 1995;Schaal et al, 2001), serine protease (Groutas et al, 2001;He et al, 2000;Kuang et al, 2000;Yang et al, 2008), metalloprotease (Ducry et al, 1999), inhibitors of noroviruses (Dou et al, 2012), glycosidase inhibitors (Benltifa et al, 2008), and antibacterial activity (Abbaz et al, 2014;Bouzina et al, 2018).…”