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Novel 9a, 11-bridged azalides : One-pot synthesis of N'-substituted 2-imino-1, 3-oxazolidines condensed to an azalide aglycone (CROSBI ID 171769)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Marušić Ištuk, Zorica ; Čikoš, Ana ; Gembarovski, Dubravka ; Lazarevski, Gorjana ; Đilović, Ivica ; Matković-Čalogović, Dubravka ; Kragol, Goran Novel 9a, 11-bridged azalides : One-pot synthesis of N'-substituted 2-imino-1, 3-oxazolidines condensed to an azalide aglycone // Bioorganic & medicinal chemistry, 19 (2011), 1; 556-566. doi: 10.1016/j.bmc.2010.10.061

Podaci o odgovornosti

Marušić Ištuk, Zorica ; Čikoš, Ana ; Gembarovski, Dubravka ; Lazarevski, Gorjana ; Đilović, Ivica ; Matković-Čalogović, Dubravka ; Kragol, Goran

engleski

Novel 9a, 11-bridged azalides : One-pot synthesis of N'-substituted 2-imino-1, 3-oxazolidines condensed to an azalide aglycone

An efficient one-pot method for the synthesis of novel 9a, 11-bridged 15-membered 9a-aza-9-deoxo-9ahomoerythromycin A and its 6-O-methyl analogue has been developed. The novel bicyclic azalide scaffold is characterized by an N'-substituted-2-imino-1, 3-oxazolidine moiety bound to a acrolactone ring between positions 9a and 11. Removal of the cladinose sugar from the starting compounds allows easy preparation of a small series of such bicyclic 3-keto and 3, 6-hemiketal azalide derivatives. A mechanism for the formation of N'-substituted-2-imino-1, 3-oxazolidines is discussed. Antibacterial properties of the prepared compounds were evaluated.

macrolide ; aAzalide ; 2-Imino-1 ; 3-oxazolidine ; Mukaiyama reagent

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Podaci o izdanju

19 (1)

2011.

556-566

objavljeno

0968-0896

10.1016/j.bmc.2010.10.061

Povezanost rada

Kemija

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