title: One-pot Ugi/Aza-Michael synthesis of highly substituted 2,5-diketopiperazines with anti-proliferative properties.
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.
authors.affiliation: Institute of Pharmacy and Food Chemistry, University of Wuerzburg, Am Hubland, 97074 Wuerzburg, Germany. andreas.hartung@uni-wuerzburg.de
authors.forename: Andreas
authors.initials: A
authors.lastname: Hartung
authors.forename: Florian
authors.initials: F
authors.lastname: Seufert
authors.forename: Carsten
authors.initials: C
authors.lastname: Berges
authors.forename: Viktoria H
authors.initials: VH
authors.lastname: Gessner
authors.forename: Ulrike
authors.initials: U
authors.lastname: Holzgrabe
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D017209:Apoptosis / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects*; D018360:Crystallography, X-Ray; D003713:Dendritic Cells / Q000378:metabolism; D054659:Diketopiperazines / Q000138:chemical synthesis*; D006801:Humans; D013601:T-Lymphocytes / Q000378:metabolism
chemical_list: D000447:Aldehydes; D000588:Amines; D054659:Diketopiperazines