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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

Academic Article
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Overview

authors

  • Sugawara, A.
  • Sunazuka, T.
  • Hirose, T.
  • Nagai, K.
  • Yamaguchi, Y.
  • Hanaki, H.
  • Sharpless, K. Barry
  • Omura, S.

publication date

  • November 2007

journal

  • Bioorganic & Medicinal Chemistry Letters  Journal

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.

subject areas

  • Anti-Bacterial Agents
  • Catalysis
  • Copper
  • Drug Design
  • Enterococcus
  • Erythromycin
  • Methicillin Resistance
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Staphylococcus aureus
  • Vancomycin Resistance
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Research

keywords

  • Anti-MRSA and -VRE agent
  • click chemistry
  • erythromycin A
  • macrolides
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Identity

International Standard Serial Number (ISSN)

  • 0960-894X

Digital Object Identifier (DOI)

  • 10.1016/j.bmcl.2007.08.068

PubMed ID

  • 17869508
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Additional Document Info

start page

  • 6340

end page

  • 6344

volume

  • 17

issue

  • 22

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