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Synthesis and antibacterial activity of C2-symmetric binaphthyl scaffolded amino acid derivatives

Journal Article


Abstract

  • The synthesis of eleven novel antibacterial agents is reported. The structures are based on a C 2-symmetric binaphthyl scaffold which holds two identical chains consisting of a short linker, a basic amino acid and a small hydrophobic side chain. Antibacterial activity is revealed for a number of derivatives down to an MIC of 2 μg/mL (2 μM) against Staphylococcus aureus - comparable to vancomycin, and an MIC of 31 μg/mL (31 μM) against some vancomycin-resistant enterococcal strains. © 2011 Elsevier Masson SAS. All rights reserved.

UOW Authors

  •   Robertson, Mark (external author)
  •   Bremner, John
  •   Coates, Jonathon A. (external author)
  •   Deadman, John (external author)
  •   Keller, Paul
  •   Pyne, Stephen
  •   Somphol, Kittiya (external author)
  •   Rhodes, David I. (external author)

Publication Date

  • 2011

Citation

  • Robertson, M., Bremner, J. B., Coates, J., Deadman, J., Keller, P. A., Pyne, S. G., Somphol, K. & Rhodes, D. I. (2011). Synthesis and antibacterial activity of C2-symmetric binaphthyl scaffolded amino acid derivatives. European Journal of Medicinal Chemistry, 46 (9), 4201-4211.

Scopus Eid

  • 2-s2.0-80052954423

Ro Metadata Url

  • http://ro.uow.edu.au/scipapers/3047

Has Global Citation Frequency

Number Of Pages

  • 10

Start Page

  • 4201

End Page

  • 4211

Volume

  • 46

Issue

  • 9

Abstract

  • The synthesis of eleven novel antibacterial agents is reported. The structures are based on a C 2-symmetric binaphthyl scaffold which holds two identical chains consisting of a short linker, a basic amino acid and a small hydrophobic side chain. Antibacterial activity is revealed for a number of derivatives down to an MIC of 2 μg/mL (2 μM) against Staphylococcus aureus - comparable to vancomycin, and an MIC of 31 μg/mL (31 μM) against some vancomycin-resistant enterococcal strains. © 2011 Elsevier Masson SAS. All rights reserved.

UOW Authors

  •   Robertson, Mark (external author)
  •   Bremner, John
  •   Coates, Jonathon A. (external author)
  •   Deadman, John (external author)
  •   Keller, Paul
  •   Pyne, Stephen
  •   Somphol, Kittiya (external author)
  •   Rhodes, David I. (external author)

Publication Date

  • 2011

Citation

  • Robertson, M., Bremner, J. B., Coates, J., Deadman, J., Keller, P. A., Pyne, S. G., Somphol, K. & Rhodes, D. I. (2011). Synthesis and antibacterial activity of C2-symmetric binaphthyl scaffolded amino acid derivatives. European Journal of Medicinal Chemistry, 46 (9), 4201-4211.

Scopus Eid

  • 2-s2.0-80052954423

Ro Metadata Url

  • http://ro.uow.edu.au/scipapers/3047

Has Global Citation Frequency

Number Of Pages

  • 10

Start Page

  • 4201

End Page

  • 4211

Volume

  • 46

Issue

  • 9