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

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

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)6340-6344
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume17
Issue number22
DOIs
Publication statusPublished - 2007 Nov 15
Externally publishedYes

Keywords

  • Anti-MRSA and -VRE agent
  • Click chemistry
  • Erythromycin A
  • Macrolides

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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