Peptidomimetics are important targets in drug discovery, because they can exhibit behavior similar to that of biologically active peptides. The need for new peptidomimetic scaffolds is important for the discovery of new therapeutics.We describe the synthesis and utility of a new class of peptidomimetics derived from both imidazolidinones and hydroxyethylene isosteres. The key step in the synthesis of this class of peptidomimetics is the ring opening/rearrangement of an a-aminoamide with fused ring aziridines. The opening with an amino amide or a peptide fragment results in an oxazolidinone intermediate, which can rearrange into an imidazolidinone. The resulting diol is converted into an aminoalcohol and then coupled with a second amino acid or peptide fragment. This provides a novel peptidomimetic containing both the well known hydroxyethyl isostere as well as an imidazolidinone.Details regarding the synthesis and utility of these peptidomimetics will be presented.

Synthesis and utility of novel peptidomimetics containing hydroxyethyl isostere and imodazolidinone

243rd National Meeting (2012)

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