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Design and synthesis via click chemistry of 8,9-anhydroerythromycin A 6,9-hemiketal analogues with anti-MRSA and -VRE activity

2007; Elsevier BV; Volume: 17; Issue: 22 Linguagem: Inglês

10.1016/j.bmcl.2007.08.068

1464-3405

Akihiro Sugawara, Toshiaki Sunazuka, Tomoyasu Hirose, Kenichiro Nagai, Yukie Yamaguchi, Hideaki Hanaki, K. Barry Sharpless, Satoshi Ōmura,

Carbohydrate Chemistry and Synthesis

An erythromycin analogue, 11,12-di-O-iso-butyryl-8,9-anhydroerythromycin A 6,9-hemiketal (1b), was found to be a potential anti-MRSA and anti-VRE agent. The use of copper catalyzed azide–acetylene cycloaddition, and click chemistry, readily provided 10 types of triazole analogues of 1b in good to nearly quantitative yield. Among the library, 5b exhibited activity against MRSA and VRE bacterial strains, representing more than twice the potency of 1b.