Synthesis and antibacterial activity of some binaphthyl-supported macrocycles containing a cationic amino acid

Daniel R. Coghlan, John B. Bremner, Paul A. Keller, Stephen G. Pyne, Dorothy M. David, Kittiya Somphol, Dean Baylis, Jonathan Coates, John Deadman, David I. Rhodes, Alan D. Robertson

Research output: Contribution to journalArticleResearchpeer-review

5 Citations (Scopus)

Abstract

As part of a programme investigating antibacterial cyclic macrocycles containing a cationic amino acid with an internal aromatic hydrophobic scaffold, we previously reported a macrocycle anchored at the 3,3′-positions of a 1,1′-binaphthyl unit. This was prepared via key intermediates containing an internal allylglycine and an allyl-substituted binaphthyl unit for a subsequent ring-closing metathesis reaction. This paper presents some structure-activity relationship studies with additional macrocycles based on this lead compound against Staphylococcus aureus together with the antibacterial activity of two related acyclic compounds.

Original languageEnglish
Pages (from-to)3549-3557
Number of pages9
JournalBioorganic & Medicinal Chemistry
Volume19
Issue number11
DOIs
Publication statusPublished - 1 Jun 2011
Externally publishedYes

Keywords

  • Anti-bacterial agents
  • Atropisomerism
  • Cyclic peptoids
  • Metathesis
  • S. aureus

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