title: Novel desosamine-modified 14- and 15-membered macrolides without antibacterial activity.
abstract: Novel modifications of the desosamine sugar of 14- and 15-membered antibacterial macrolides, in which the desosamine was fused with N-substituted-1,3-oxazolidin-2-ones, were developed in order to completely suppress antibacterial activity and make them promising agents for other biological targets. The synthesis of such bicyclic desosamine derivatives, especially 1,3-oxazolidin-2-one formation, was optimized and conducted under mild conditions without a need for protection/deprotection steps for other functional groups. A focused series of novel desosamine-modified macrolide derivatives was prepared and their antibacterial activities tested. It was shown that these macrolide derivatives do not possess any residual antibacterial activity.
authors.affiliation: GlaxoSmithKline Research Centre Zagreb, Zagreb, Croatia.
authors.forename: Ivana Palej
authors.initials: IP
authors.lastname: Jakopović
authors.forename: Mirjana Bukvić
authors.initials: MB
authors.lastname: Krajačić
authors.forename: Maja Matanović
authors.initials: MM
authors.lastname: Skugor
authors.forename: Vlado
authors.initials: V
authors.lastname: Stimac
authors.forename: Dijana
authors.initials: D
authors.lastname: Pešić
authors.forename: Ines
authors.initials: I
authors.lastname: Vujasinović
authors.forename: Sulejman
authors.initials: S
authors.lastname: Alihodžić
authors.forename: Hana
authors.initials: H
authors.lastname: Čipčić Paljetak
authors.forename: Goran
authors.initials: G
authors.lastname: Kragol
mesh_terms: D000606:Amino Sugars / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D003500:Cyclization
chemical_list: D000606:Amino Sugars; D000900:Anti-Bacterial Agents; C110125:desosamine