Dendroid Peptide Structural Mimetics of ω-Conotoxin MVIIA based on a 2(1H)-Quinolinone Core

Three mimetics of the peptide ω-Conotoxin MVIIA have been synthesised following the dendroid approach. The three key central amino acids of the natural peptide are mimicked by phenylguanidine (arginine), isopentyl (leucine) and aryl alcohol (tyrosine) attached to a quinolinone core at the 1- and 8-positions. The derivatives are designed to position these key groups in similar spatial orientation to that of the natural peptide in a structure that will have limited conformational flexibility. Key steps of the syntheses involve selective N-alkylation of quinolinone derivatives and guanylation of aryl amines.