Potential of amino acid-derived α-amino nitriles for generating molecular diversity

Abstract

This review covers some of the contributions of the authors to the peptidomimetic field. These contributions explore the potential of amino acid-derived α-amino nitriles for generating molecular diversity. Cyanomethyleneamino pseudopeptide analogues of several bioactive peptides and α-quaternary amino nitriles were obtained via a modified three component Strecker synthesis. Taking advantage of the reactivity of the cyano group and the diverse functionality of amino acid derivatives, cyanomethyleneamino pseudopeptides were transformed into carbamoylmethyleneamino and branched pseudopeptides or privileged heterocyclic scaffolds, such as: piperazine, pyrazino[1,2-c]pyrimidine, 1,4- benzodiazepine, and novel indole derivatives, including some spirocyclic compounds.