One-Pot Ugi/Aza-Michael Synthesis of Highly Substituted 2,5-Diketopiperazines with Anti-Proliferative Properties

One-Pot Ugi/Aza-Michael Synthesis of Highly Substituted 2,5-Diketopiperazines with Anti-Proliferative Properties

The well-known Ugi reaction of aldehydes with amines, carboxylic acids and isocyanides leads to the formation of acyclic α-acylaminocarboxamides. Replacement of the carboxylic acid derivatives with β-acyl substituted acrylic acids gives access to highly substituted 2,5-dike...

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Bibliographic Details
Main Authors: Ulrike Holzgrabe, Viktoria H. Gessner, Florian Seufert, Carsten Berges, Andreas Hartung
Format: Article
Language:English
Published: MDPI AG 2012-12-01
Series:Molecules
Subjects:
multicomponent Ugi-type reaction
intramolecular Michael addition
2,5-diketopiperazines
anti-proliferative effects
Online Access:http://www.mdpi.com/1420-3049/17/12/14685
Description
Summary:The well-known Ugi reaction of aldehydes with amines, carboxylic acids and isocyanides leads to the formation of acyclic α-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.
ISSN:1420-3049

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