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Molecules 2012, 17(12), 14685-14699; doi:10.3390/molecules171214685
Article

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

1
,
1
,
2
,
3
 and
1,*
1 Institute of Pharmacy and Food Chemistry, University of Wuerzburg, Am Hubland, 97074 Wuerzburg, Germany 2 Department of Internal Medicine II, Translational Immunotherapy, University Hospital Wuerzburg, Versbacherstr 5, 97078 Wuerzburg, Germany 3 Institute of Inorganic Chemistry, University of Wuerzburg, Am Hubland, 97074 Wuerzburg, Germany
* Author to whom correspondence should be addressed.
Received: 21 November 2012 / Revised: 1 December 2012 / Accepted: 6 December 2012 / Published: 11 December 2012
(This article belongs to the Special Issue Multicomponent Reaction)
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Abstract

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.
Keywords: multicomponent Ugi-type reaction; intramolecular Michael addition; 2,5-diketopiperazines; anti-proliferative effects multicomponent Ugi-type reaction; intramolecular Michael addition; 2,5-diketopiperazines; anti-proliferative effects
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Hartung, A.; Seufert, F.; Berges, C.; Gessner, V.H.; Holzgrabe, U. One-Pot Ugi/Aza-Michael Synthesis of Highly Substituted 2,5-Diketopiperazines with Anti-Proliferative Properties. Molecules 2012, 17, 14685-14699.

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