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Novel desosamine-modified 14- and 15-membered macrolides without antibacterial activity

2012; Elsevier BV; Volume: 22; Issue: 10 Linguagem: Inglês

10.1016/j.bmcl.2012.03.076

1464-3405

Ivana Palej Jakopović, Mirjana Bukvić Krajačić, Maja Matanović Škugor, Vlado Štimac, Dijana Pešić, Ines Vujasinović, Sulejman Alihodžić, Hana Čipčić Paljetak, Goran Kragol,

Antibiotic Resistance in Bacteria

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.