Synthesis and antibacterial studies of binaphthyl-based tripeptoids. Part 2 |
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Authors: | John B Bremner Paul A Keller Stephen G Pyne Timothy P Boyle Zinka Brkic Jody Morgan Kittiya Somphol Jonathan A Coates John Deadman David I Rhodes |
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Institution: | 1. School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia;2. Avexa Ltd, 576 Swan St, Richmond, Vic. 3121, Australia |
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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 μg/mL). The biphenyl analogue also showed good activity against S. aureus (MIC 1.95 μg/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. |
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