Synthesis and antibacterial studies of binaphthyl-based tripeptoids. Part 2.
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.
Bremner
John B
JB
School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia.
Keller
Paul A
PA
Pyne
Stephen G
SG
Boyle
Timothy P
TP
Brkic
Zinka
Z
Morgan
Jody
J
Somphol
Kittiya
K
Coates
Jonathan A
JA
Deadman
John
J
Rhodes
David I
DI
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D016983:Enterococcus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D009281:Naphthalenes / Q000737:chemistry*; D034444:Peptoids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D020713:Vancomycin Resistance
D000900:Anti-Bacterial Agents; D009281:Naphthalenes; D034444:Peptoids; C031721:naphthalene