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Synthesis and antibacterial studies of binaphthyl-based tripeptoids. Part 2

Journal Article


Abstract


  • A compact synthesis of 15 new binaphthyl-based dicationic tripeptoids and one biphenyl based dicationic tripeptoid is described. Fourteen of these tripeptoids resulted from variation of the C-2' ether substituent of the binaphthyl unit. An O-iso-butyl ether binaphthyl derivative was found to be the most active against Staphylococcus aureus (MIC 1.95 mu g/mL). The biphenyl analogue also showed good activity against S. aureus (MIC 1.95 mu g/mL). These compounds, however, were less active against four vancomycin-resistant strains of enterococci (VRE) than some of our previously developed compounds that had an O-iso-pentyl ether substituent on the binaphthyl unit and a C-2 L-Leu moiety. (C) 2010 Elsevier Ltd. All rights reserved.

Publication Date


  • 2010

Citation


  • Bremner, J. B., Keller, P. A., Pyne, S. G., Boyle, T. P., Brkic, Z., Morgan, J., Somphol, K., Coates, J., Deadman, J. & Rhodes, D. I. (2010). Synthesis and antibacterial studies of binaphthyl-based tripeptoids. Part 2. Bioorganic and Medicinal Chemistry, 18 (13), 4793-4800.

Scopus Eid


  • 2-s2.0-77954214959

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/5086

Has Global Citation Frequency


Number Of Pages


  • 7

Start Page


  • 4793

End Page


  • 4800

Volume


  • 18

Issue


  • 13

Abstract


  • A compact synthesis of 15 new binaphthyl-based dicationic tripeptoids and one biphenyl based dicationic tripeptoid is described. Fourteen of these tripeptoids resulted from variation of the C-2' ether substituent of the binaphthyl unit. An O-iso-butyl ether binaphthyl derivative was found to be the most active against Staphylococcus aureus (MIC 1.95 mu g/mL). The biphenyl analogue also showed good activity against S. aureus (MIC 1.95 mu g/mL). These compounds, however, were less active against four vancomycin-resistant strains of enterococci (VRE) than some of our previously developed compounds that had an O-iso-pentyl ether substituent on the binaphthyl unit and a C-2 L-Leu moiety. (C) 2010 Elsevier Ltd. All rights reserved.

Publication Date


  • 2010

Citation


  • Bremner, J. B., Keller, P. A., Pyne, S. G., Boyle, T. P., Brkic, Z., Morgan, J., Somphol, K., Coates, J., Deadman, J. & Rhodes, D. I. (2010). Synthesis and antibacterial studies of binaphthyl-based tripeptoids. Part 2. Bioorganic and Medicinal Chemistry, 18 (13), 4793-4800.

Scopus Eid


  • 2-s2.0-77954214959

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/5086

Has Global Citation Frequency


Number Of Pages


  • 7

Start Page


  • 4793

End Page


  • 4800

Volume


  • 18

Issue


  • 13