Synthesis and antibacterial activity of new chiral N-sulfamoyloxazolidin-2-ones

Bouchareb, Fouzia; Berredjem, Malika; Kaki, Samira Ait; Bouaricha, Amel; Bouzina, Abdeslem; Belhani, Billel; Aouf, Nour‐Eddine

doi:10.1007/s12039-015-1004-x

Cited by 9 publications

(8 citation statements)

References 25 publications

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“…Chlorohydrins and ECH were used to prepare derivatives of pyridine [139][140][141], phtalazines [142][143][144], oxazolidinone [122,145,146], triazinones [147], thioglycoside [148] and aziridines [149]. N-Heterocycles have wide applicability as antibiotics [150][151][152].…”

Section: Funcionalization Of Aza-heterocyclic Compoundsmentioning

confidence: 99%

“…The synthesis of oxazolidinones was described by using 1,3-DCH [145,146], or 1,3-dichloropropan-2-yl esters [118]. Figure 23 shows the synthesis of oxozalidinones, starting from 1,3-dichloropropan-2-yl esters described by the authors' research group [118].…”

Section: Synthesis Of Oxazolidinonesmentioning

confidence: 99%

“…Alternatively, the reaction between the carbamate and amines led to substituted sulfamides. Finally, the carboxylsulfamides in presence of potassium carbonate in acetonitrile led to 5-chloromethyl-2-oxazolidinone sulphonamides with a chiral center at the 5-position (90% to 98% yield) ( Figure 24, R 1 ) [145,146]. The antibacterial activity of these compounds was evaluated.…”

Section: Synthesis Of Oxazolidinonesmentioning

confidence: 99%

“…The antibacterial activity of these compounds was evaluated. Most of the compounds showed moderate-to-good antibacterial activity [145]. N-acyl migration ( Figure 23) [120].…”

Section: Synthesis Of Oxazolidinonesmentioning

confidence: 99%

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Preparation and Uses of Chlorinated Glycerol Derivatives

et al. 2020

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Crude glycerol (C3H8O3) is a major by-product of biodiesel production from vegetable oils and animal fats. The increased biodiesel production in the last two decades has forced glycerol production up and prices down. However, crude glycerol from biodiesel production is not of adequate purity for industrial uses, including food, cosmetics and pharmaceuticals. The purification process of crude glycerol to reach the quality standards required by industry is expensive and dificult. Novel uses for crude glycerol can reduce the price of biodiesel and make it an economical alternative to diesel. Moreover, novel uses may improve environmental impact, since crude glycerol disposal is expensive and dificult. Glycerol is a versatile molecule with many potential applications in fermentation processes and synthetic chemistry. It serves as a glucose substitute in microbial growth media and as a precursor in the synthesis of a number of commercial intermediates or fine chemicals. Chlorinated derivatives of glycerol are an important class of such chemicals. The main focus of this review is the conversion of glycerol to chlorinated derivatives, such as epichlorohydrin and chlorohydrins, and their further use in the synthesis of additional downstream products. Downstream products include non-cyclic compounds with allyl, nitrile, azide and other functional groups, as well as oxazolidinones and triazoles, which are cyclic compounds derived from ephichlorohydrin and chlorohydrins. The polymers and ionic liquids, which use glycerol as an initial building block, are highlighted, as well.

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Section: Funcionalization Of Aza-heterocyclic Compoundsmentioning

confidence: 99%

Section: Synthesis Of Oxazolidinonesmentioning

confidence: 99%

Section: Synthesis Of Oxazolidinonesmentioning

confidence: 99%

“…The antibacterial activity of these compounds was evaluated. Most of the compounds showed moderate-to-good antibacterial activity [145]. N-acyl migration ( Figure 23) [120].…”

Section: Synthesis Of Oxazolidinonesmentioning

confidence: 99%

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Preparation and Uses of Chlorinated Glycerol Derivatives

et al. 2020

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“…In continuation of our interest in the preparation of sulfonamide and sulfamide derivatives [ 28 , 29 , 30 , 31 ], we decided to include both motifs, sulfamido and phosphonate, on each targeted compound and then to obtain new hybrids also containing an α-phenyl on the phosphonate methylene. For this preliminary study, we opted to select a set of various substituents -NR 2 R 3 and -PO(OR 1 ) 2 in order to shape the first SAR trends in this series ( Figure 3 ).…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2018

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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.

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Potential antibacterial and antifungal activities of novel sulfamidophosphonate derivatives bearing the quinoline or quinolone moiety

Bazine

Bendjedid²,

Boukhari

2020

Archiv der Pharmazie

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A series of new α‐sulfamidophosphonate/sulfonamidophosphonate ( 4a – n ) and cyclosulfamidophosphonate ( 5a – d ) derivatives containing the quinoline or quinolone moiety was designed and synthesized via Kabachnik–Fields reaction in the presence of ionic liquid under ultrasound irradiation. This efficient methodology provides new 1,2,5‐thiadiazolidine‐1,1‐dioxide derivatives 5a – d in one step and optimal conditions. The molecular structures of the novel compounds 4a – n and 5a – d were confirmed using various spectroscopic methods. All these compounds were evaluated for their in vitro antibacterial activity against Gram‐negative ( Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) and Gram‐positive ( Staphylococcus aureus ATCC 27923) bacteria, in addition to three clinical strains ( E. coli 1, P. aeruginosa 1, and S. aureus 1). Most of the tested compounds showed more potent inhibitory activities against both Gram‐positive and ‐negative bacteria compared with the sulfamethoxazole reference. The following compounds, 4n , 4f , 4g , 4m , 4l , 4d , and 4e , are the most active sulfamidophosphonate derivatives. Furthermore, these molecules gave interesting zones of inhibition varying between 28 and 49 mm, against all tested bacterial strains, with a low minimum inhibitory concentration (MIC) value ranging from 0.125 to 8 μg/ml. All the synthesized derivatives were also evaluated for their in vitro antifungal activity against Fusarium oxyporum f. sp. lycopersici and Alternaria sp. The results revealed that all the synthesized compounds exhibited excellent antifungal inhibition and the compounds 4f , 4g , 4m , and 4i were the most potent derivatives with MIC values ranging from 0.25 to 1 µg/ml against the two tested fungal strains. The strongest inhibition of bacteria and fungi strains was detected by the effect of quinolone and sulfamide moieties.

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Synthesis and antibacterial activity of new chiral N-sulfamoyloxazolidin-2-ones

Cited by 9 publications

References 25 publications

Preparation and Uses of Chlorinated Glycerol Derivatives

Preparation and Uses of Chlorinated Glycerol Derivatives

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

Potential antibacterial and antifungal activities of novel sulfamidophosphonate derivatives bearing the quinoline or quinolone moiety

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