Synthesis and antibacterial activity of novel modified 5-O-mycaminose 14-membered ketolides

•A method of modifying the C-4′ position of 14-membered ketolides was developed.•Several modified 5-O-4′-carbamate mycaminose ketolides were designed and synthesized.•Antibacterial activities of all the target compounds were evaluated.•18e showed comparable activity to telithromycin and clarithromycin.•The others displayed weak antibacterial activity.

A practicable method of introducing a side chain to the C-4′ position of 5-O-desosamine in the 14-membered ketolides was developed. And using this method, a series of novel modified 5-O-mycaminose ketolides were synthesized. These ketolides containing 5-O-4′-carbamate mycaminose were evaluated for their in vitro antibacterial activities against some respiratory pathogens. 15b and 18e showed comparable activity to telithromycin and clarithromycin.

Graphical abstractA series of novel modified 5-O-mycaminose 14-membered ketolides were synthesized and evaluated for their antibacterial activities.Figure optionsDownload full-size imageDownload as PowerPoint slide