Dendroid peptide structural mimetics of omega-conotoxin MVIIA based on a 2(1H)-quinolinone core

Three mimetics of the peptide omega-Conotoxin MVIIA have been synthesised f ollowing the dendroid approach. The three key central amino acids of the na tural peptide are mimicked by phenylguanidine (arginine), isopentyl (leucin e) 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 t hat will have limited conformational flexibility. Key steps of the synthese s involve selective N-alkylation of quinolinone derivatives and guanylation of aryl amines. (C) 2000 Elsevier Science Ltd. All rights reserved.