Synthesis and antibacterial activity of some binaphthyl-supported macrocycles containing a cationic amino acid

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.

Twelve macrocyclic derivatives with anti-bacterial activity against Staphylococcus aureus are reported.Figure optionsDownload as PowerPoint slide