Synthesis of perhydrodiazepinones as new putative peptidomimetics

Abstract

New functionalized 7-membered azaheterocycles (perhydrodiazepinones) have been designed as new scaffolds supposed to mimick peptide γ-turns constrained by an ethylene bridge. They were synthesized by either lactam cyclisation on an aminoacid compound outcoming from a glutamic acid derivative starting material or through an intramolecular Mitsunobu reaction on diaminoalcohol linear precursors. Furthermore, as a new strategy useful for combinatorial chemistry, the second synthesis has been investigated on a soluble polymer support (PEG).