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

Molecules

Andreas Hartung¹  Florian Seufert¹  Carsten Berges¹  Viktoria H. Gessner¹ 

[1] ¹Institute of Pharmacy and Food Chemistry, University of Wuerzburg, Am Hubland, 97074 Wuerzburg, Germany ²Department of Internal Medicine II, Translational Immunotherapy, University Hospital Wuerzburg, Versbacherstr 5, 97078 Wuerzburg, Germany ³Institute of Inorganic Chemistry, University of Wuerzburg, Am Hubland, 97074 Wuerzburg, Germany

关键词: multicomponent Ugi-type reaction;    intramolecular Michael addition;    2;    5-diketopiperazines;    anti-proliferative effects;   

DOI  :  10.3390/molecules171214685

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.