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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.

SUBMITTER: Bouzina A 

PROVIDER: S-EPMC6099799 | biostudies-other | 2018 Jul

REPOSITORIES: biostudies-other

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Synthesis, Spectroscopic Characterization, and <i>In Vitro</i> Antibacterial Evaluation of Novel Functionalized Sulfamidocarbonyloxyphosphonates.

Bouzina Abdeslem A   Bechlem Khaoula K   Berredjem Hajira H   Belhani Billel B   Becheker Imène I   Lebreton Jacques J   Le Borgne Marc M   Bouaziz Zouhair Z   Marminon Christelle C   Berredjem Malika M  

Molecules (Basel, Switzerland) 20180710 7


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, <sup>13</sup>C, and <sup>31</sup>P NMR spectroscopy, IR spectroscopy, and mass spectroscopy, as well as elemental analysis. Eight compounds were evaluated for their <i>in  ...[more]

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