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

Journal Article


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. © 2011 Elsevier Ltd. All rights reserved.

Authors


  •   Coghlan, Daniel (external author)
  •   Bremner, John B.
  •   Keller, Paul A.
  •   Pyne, Stephen G.
  •   David, Dorothy (external author)
  •   Somphol, Kittiya (external author)
  •   Baylis, Dean (external author)
  •   Coates, Jonathon A. (external author)
  •   Deadman, John (external author)
  •   Rhodes, David I. (external author)
  •   Robertson, A D (external author)

Publication Date


  • 2011

Citation


  • Coghlan, D. R., Bremner, J. B., Keller, P. A., Pyne, S. G., David, D. M., Somphol, K., Baylis, D., Coates, J., Deadman, J., Rhodes, D. I. & Robertson, A. D. (2011). Synthesis and antibacterial activity of some binaphthyl-supported macrocycles containing a cationic amino acid. Bioorganic and Medicinal Chemistry, 19 (11), 3549-3557.

Scopus Eid


  • 2-s2.0-79957471147

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/3458

Number Of Pages


  • 8

Start Page


  • 3549

End Page


  • 3557

Volume


  • 19

Issue


  • 11

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. © 2011 Elsevier Ltd. All rights reserved.

Authors


  •   Coghlan, Daniel (external author)
  •   Bremner, John B.
  •   Keller, Paul A.
  •   Pyne, Stephen G.
  •   David, Dorothy (external author)
  •   Somphol, Kittiya (external author)
  •   Baylis, Dean (external author)
  •   Coates, Jonathon A. (external author)
  •   Deadman, John (external author)
  •   Rhodes, David I. (external author)
  •   Robertson, A D (external author)

Publication Date


  • 2011

Citation


  • Coghlan, D. R., Bremner, J. B., Keller, P. A., Pyne, S. G., David, D. M., Somphol, K., Baylis, D., Coates, J., Deadman, J., Rhodes, D. I. & Robertson, A. D. (2011). Synthesis and antibacterial activity of some binaphthyl-supported macrocycles containing a cationic amino acid. Bioorganic and Medicinal Chemistry, 19 (11), 3549-3557.

Scopus Eid


  • 2-s2.0-79957471147

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/3458

Number Of Pages


  • 8

Start Page


  • 3549

End Page


  • 3557

Volume


  • 19

Issue


  • 11