title: Synthesis and antibacterial activity of some binaphthyl-supported macrocycles containing a cationic amino acid.
abstract: As part of a programme investigating antibacterial cyclic macrocycles containing a cationic amino acid with an internal aromatic hydrophobic scaffold, we previously reported a macrocycle anchored at the 3,3'-positions of a 1,1'-binaphthyl unit. This was prepared via key intermediates containing an internal allylglycine and an allyl-substituted binaphthyl unit for a subsequent ring-closing metathesis reaction. This paper presents some structure-activity relationship studies with additional macrocycles based on this lead compound against Staphylococcus aureus together with the antibacterial activity of two related acyclic compounds.
authors.affiliation: School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia.
authors.forename: Daniel R
authors.initials: DR
authors.lastname: Coghlan
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: Dorothy M
authors.initials: DM
authors.lastname: David
authors.forename: Kittiya
authors.initials: K
authors.lastname: Somphol
authors.forename: Dean
authors.initials: D
authors.lastname: Baylis
authors.forename: Jonathan
authors.initials: J
authors.lastname: Coates
authors.forename: John
authors.initials: J
authors.lastname: Deadman
authors.forename: David I
authors.initials: DI
authors.lastname: Rhodes
authors.forename: Alan D
authors.initials: AD
authors.lastname: Robertson
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002412:Cations / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000596:Amino Acids; D000900:Anti-Bacterial Agents; D002412:Cations; D047028:Macrocyclic Compounds