Synthesis and antibacterial activities of 5-hydroxy-4-amino-2(5H)-furanones.
Starting from the mucohalogen acids 1a and b 5-hydroxy-2(5H)-furanones 2a-h have been prepared and tested. These novel 4-amino-5-hydroxy 2(5H)-furananones have shown a broad antibiotic activity against Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853 in the micromolar range. A one step synthesis from mucohalogen acids towards the antibacterials 2a-h was developed, in which the target was obtained from 1a and b under reflux in toluene in presence of a catalytic amount of sulfuric acid. The derivatives 2b and c displayed a MIC and MBC of 4/8mug/ml, against Staphylococcus aureus with a selectivity towards the resistant strains.
Lattmann
Eric
E
Aston Pharmacy School, Aston University, Birmingham B4 7ET, England. e.lattmann@aston.ac.uk
Dunn
Simon
S
Niamsanit
Suwanna
S
Sattayasai
Nison
N
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D024881:Drug Resistance, Bacterial; D004926:Escherichia coli / Q000187:drug effects; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects
D000900:Anti-Bacterial Agents; D005663:Furans