title: Synthesis and antibacterial studies of binaphthyl-based tripeptoids. Part 2.
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.
authors.affiliation: School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia.
authors.forename: John B
authors.initials: JB
authors.lastname: Bremner
authors.forename: Paul A
authors.initials: PA
authors.lastname: Keller
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Pyne
authors.forename: Timothy P
authors.initials: TP
authors.lastname: Boyle
authors.forename: Zinka
authors.initials: Z
authors.lastname: Brkic
authors.forename: Jody
authors.initials: J
authors.lastname: Morgan
authors.forename: Kittiya
authors.initials: K
authors.lastname: Somphol
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Coates
authors.forename: John
authors.initials: J
authors.lastname: Deadman
authors.forename: David I
authors.initials: DI
authors.lastname: Rhodes
mesh_terms: 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
chemical_list: D000900:Anti-Bacterial Agents; D009281:Naphthalenes; D034444:Peptoids; C031721:naphthalene