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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 ?-acylaminocarboxamides. Replacement of the carboxylic acid derivatives with ?-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.

SUBMITTER: Hartung A

PROVIDER: S-EPMC6268348 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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One-pot Ugi/Aza-Michael synthesis of highly substituted 2,5-diketopiperazines with anti-proliferative properties.

Hartung Andreas A Seufert Florian F Berges Carsten C Gessner Viktoria H VH Holzgrabe Ulrike U

Molecules (Basel, Switzerland) 20121211 12

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 t ...[more]

PMID: 23519247

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