Copper(I/II)-Promoted Diverse Imidazo[1,2-α]pyridine Synthesis on Solid-Phase Bound DNA Oligonucleotides for Encoded Library Design.


Journal

Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393

Informations de publication

Date de publication:
16 07 2021
Historique:
pubmed: 29 6 2021
medline: 15 12 2021
entrez: 28 6 2021
Statut: ppublish

Résumé

DNA-encoded libraries designed around heterocyclic scaffolds have proven highly productive in target-based screening. Here, we show the synthesis of imidazopyridines on a controlled pore glass-coupled DNA oligonucleotide for solid phase-initiated encoded library synthesis. The target compounds were synthesized by a variant of the A3 coupling reaction from aminopyridines, alkynes, and aldehydes promoted by copper(I/II) and furnished diverse substituted scaffolds with functionalities for library design. Although proceeding under forcing conditions, it produced minimal DNA damage.

Identifiants

pubmed: 34181416
doi: 10.1021/acs.orglett.1c01834
doi:

Substances chimiques

Alkynes 0
Imidazoles 0
Oligonucleotides 0
Pyridines 0
imidazopyridine 0
Copper 789U1901C5

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

5480-5484

Auteurs

Marco Potowski (M)

Faculty of Chemistry and Chemical Biology, Medicinal Chemistry, TU Dortmund University, Otto-Hahn-Str. 6, 44227 Dortmund, Germany.

Ricarda Lüttig (R)

Faculty of Chemistry and Chemical Biology, Medicinal Chemistry, TU Dortmund University, Otto-Hahn-Str. 6, 44227 Dortmund, Germany.

Alexandros Vakalopoulos (A)

Medicinal Chemistry, Bayer AG, Aprather Weg 18a, 42096 Wuppertal, Germany.

Andreas Brunschweiger (A)

Faculty of Chemistry and Chemical Biology, Medicinal Chemistry, TU Dortmund University, Otto-Hahn-Str. 6, 44227 Dortmund, Germany.

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Classifications MeSH