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

Bioorganic & Medicinal Chemistry
John B BremnerDavid I Rhodes

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.

References

May 12, 2007·Trends in Molecular Medicine·Gerard D Wright, Arlene D Sutherland
Mar 20, 2010·Bioorganic & Medicinal Chemistry·John B BremnerDavid I Rhodes

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