Next Article in Journal
New Advances in Titanium-Mediated Free Radical Reactions
Previous Article in Journal
Wu-Chia-Pi Solution Attenuates Carbon Tetrachloride-Induced Hepatic Injury through the Antioxidative Abilities of Its Components Acteoside and Quercetin
Previous Article in Special Issue
Multicomponent Synthesis of 3,6-Dihydro-2H-1,3-thiazine-2-thiones
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,*
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)
Download PDF [333 KB, uploaded 18 June 2014]
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


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.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert