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

Andreas Hartung 1 email, Florian Seufert 1 email, Carsten Berges 2 email, Viktoria H. Gessner 3 email and Ulrike Holzgrabe 1,* email
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; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

Hartung A, Seufert F, Berges C, Gessner VH, Holzgrabe U. One-Pot Ugi/Aza-Michael Synthesis of Highly Substituted 2,5-Diketopiperazines with Anti-Proliferative Properties. Molecules. 2012; 17(12):14685-14699.

Chicago/Turabian Style

Hartung, Andreas; Seufert, Florian; Berges, Carsten; Gessner, Viktoria H.; Holzgrabe, Ulrike. 2012. "One-Pot Ugi/Aza-Michael Synthesis of Highly Substituted 2,5-Diketopiperazines with Anti-Proliferative Properties." Molecules 17, no. 12: 14685-14699.

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