One-Pot ugi/aza-michael synthesis of highly substituted 2,5-diketopiperazines with anti-proliferative properties

Abstract

The well-known Ugi reaction of aldehydes with amines, carboxylic acids and isocyanides leads to the formation of acyclic a-acylaminocarboxamides. Replacement of the carboxylic acid derivatives with β-acyl substituted acrylic acids gives access to highly substituted 2,5-diketopiperazines in one single reaction-step without additives or complex reaction procedures. The obtained diketopiperazines show anti-proliferative effects on activated T cells and represent therefore potential candidates for targeting unwanted T cell-mediated immune responses. © 2012 by the authors; licensee MDPI, Basel, Switzerland.