jo061758p_si_003.cif (10.8 kB)
Convergent Synthesis of Complex Diketopiperazines Derived from Pipecolic Acid Scaffolds and Parallel Screening against GPCR Targets
dataset
posted on 2006-11-10, 00:00 authored by Sivaraman Dandapani, Ping Lan, Aaron B. Beeler, Scott Beischel, Athier Abbas, Bryan L. Roth, John A. Porco,, James S. PanekA 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).