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

Please always quote using this URN: urn:nbn:de:bvb:20-opus-130423
  • The well-known Ugi reaction of aldehydes with amines, carboxylic acids and isocyanides leads to the formation of acyclic alpha-acylaminocarboxamides. Replacement of the carboxylic acid derivatives with beta-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 immuneThe well-known Ugi reaction of aldehydes with amines, carboxylic acids and isocyanides leads to the formation of acyclic alpha-acylaminocarboxamides. Replacement of the carboxylic acid derivatives with beta-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.show moreshow less

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Metadaten
Author: Andreas Hartung, Florian Seufert, Carsten Berges, Viktoria H. Gessner, Ulrike Holzgrabe
URN:urn:nbn:de:bvb:20-opus-130423
Document Type:Journal article
Faculties:Medizinische Fakultät / Medizinische Klinik und Poliklinik II
Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie
Fakultät für Chemie und Pharmazie / Institut für Pharmazie und Lebensmittelchemie
Language:English
Parent Title (English):Molecules
Year of Completion:2012
Volume:17
Issue:12
Pagenumber:14685-14699
Source:Molecules 2012, 17, 14685-14699; doi:10.3390/molecules171214685
DOI:https://doi.org/10.3390/molecules171214685
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Tag:2,5-diketopiperazines; T cell; anti-proliferative effects; chemistry; derivates; diketopiperazines; intramolecular Michael addition; multicomponent Ugi-type reaction; strategy
Release Date:2016/11/28
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung