Parallel Synthesis and Biological Screening of Dopamine Receptor Ligands Taking Advantage of a Click Chemistry Based BAL Linker
- 25 January 2005
- journal article
- Published by American Chemical Society (ACS) in Journal of Combinatorial Chemistry
- Vol. 7 (2) , 309-316
- https://doi.org/10.1021/cc049860s
Abstract
The click-chemistry-derived formyl indolyl methyl triazole (FIMT) resin 1a was evaluated for the parallel solid-phase synthesis of a series of BP-897-type arylcarboxamides. By application of a five-step sequence (including loading by reductive amination, subsequent amide coupling, deprotection, palladium-catalyzed N-arylation, and acidic cleavage), a focused library of putative dopamine D3 receptor ligands was constructed. The final products revealed good to excellent purity and were screened for binding at monoaminergic G-protein-coupled receptors when selected library members proved to show excellent binding affinity, especially toward the dopamine D3 receptor subtype.Keywords
This publication has 16 references indexed in Scilit:
- Solid-Phase Synthesis of Lidocaine and Procainamide Analogues Using Backbone Amide Linker (BAL) AnchoringJournal of Combinatorial Chemistry, 2003
- BAL resin for the preparation of secondary aminesTetrahedron Letters, 2003
- Click Linker: Efficient and High-Yielding Synthesis of a New Family of SPOS Resins by 1,3-Dipolar CycloadditionOrganic Letters, 2003
- Palladium-Catalyzed Amination of Aryl Halides on Solid SupportOrganic Letters, 2002
- The Ortho Backbone Amide Linker (o-BAL) Is an Easily Prepared and Highly Acid-Labile Handle for Solid-Phase SynthesisJournal of Combinatorial Chemistry, 2002
- Solid-phase synthesis of C-terminal peptide aldehydes from amino acetals anchored to a backbone amide linker (BAL) handleTetrahedron Letters, 2000
- Backbone Amide Linker (BAL) Strategy forNα-9-Fluorenylmethoxycarbonyl (Fmoc) Solid-Phase Synthesis of Unprotected Peptidep-Nitroanilides and Thioesters1The Journal of Organic Chemistry, 1999
- Indole Resin: A Versatile New Support for the Solid-Phase Synthesis of Organic MoleculesThe Journal of Organic Chemistry, 1998
- Secondary amide-based linkers for solid phase organic synthesisTetrahedron Letters, 1997
- AMEBA: An acid sensitive aldehyde resin for solid phase synthesisTetrahedron Letters, 1997