Convergent synthesis of complex diketopiperazines derived from pipecolic acid scaffolds and parallel screening against GPCR targets

Sivaraman Dandapani, Ping Lan, Aaron B. Beeler, Scott Beischel, Athier Abbas, Bryan L. Roth, John A. Porco, James S. Panek

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

A convergent approach to highly functionalized diketopiperazines (DKPs) using enantioenriched pipecolic acids is described. Scandium triflate-catalyzed [4 + 2] aza-annulation was employed to produce stereochemically well-defined building blocks. A resin "catch and release" strategy was devised to convert annulation products to pipecolic acid monomers. Complex diketopiperazines were efficiently assembled utilizing one-pot cyclodimerization of pipecolic acids. Massively parallel screening of the complex DKPs against a panel of molecular targets identified novel ligands for a number of G-protein-coupled receptors (GPCRs).

Original languageEnglish (US)
Pages (from-to)8934-8945
Number of pages12
JournalJournal of Organic Chemistry
Volume71
Issue number23
DOIs
StatePublished - Nov 10 2006
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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