title: Synthesis and antibacterial activity of novel neamine derivatives: preponderant role of the substituent position on the neamine core.
abstract: A series of neamine derivatives were prepared from the cyclic carbonate and sulfate of 1,3,2',6'-tetraazido-3',4',-di-O-acetylneamine. Ring opening reactions with diversely substituted amines result in the formation of the corresponding carbamates or sulfonic acids with good overall yields. The antibacterial activities of the synthesized products against E. coli (DH5α) and S. aureus (RN4220) were evaluated. With isolated single regioisomers, the preponderant effect of the 5-positions of the carbamate substituent on the neamine core was demonstrated.
authors.affiliation: Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Gernigon
authors.forename: Valérie
authors.initials: V
authors.lastname: Bordeau
authors.forename: Fabienne
authors.initials: F
authors.lastname: Berrée
authors.forename: Brice
authors.initials: B
authors.lastname: Felden
authors.forename: Bertrand
authors.initials: B
authors.lastname: Carboni
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D005601:Framycetin / Q000737:chemistry* / Q000494:pharmacology; D050296:Microbial Viability / Q000187:drug effects; D015394:Molecular Structure; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D005601:Framycetin; C488396:neamine