Pyridine-Fused 2-Pyridones via Povarov and A3 Reactions: Rapid Generation of Highly Functionalized Tricyclic Heterocycles Capable of Amyloid Fibril Binding

Pardeep Singh, Dan E. Adolfsson, Jörgen Ådén, Andrew G. Cairns, Christian Bartens, Kristoffer Brännström, Anders Olofsson, Fredrik Almqvist (Lead / Corresponding author)

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

We here describe the use of three-component reactions to synthesize tricyclic pyridine ring-fused 2-pyridones. The developed protocols have a wide substrate scope and allow for the installation of diverse chemical functionalities on the tricyclic central fragment. Several of these pyridine-fused rigid polyheterocycles are shown to bind to Aβ and α-synuclein fibrils, which are associated with neurodegenerative diseases.

Original languageEnglish
Pages (from-to)3887-3903
Number of pages17
JournalJournal of Organic Chemistry
Volume84
Issue number7
Early online date13 Mar 2019
DOIs
Publication statusPublished - 5 Apr 2019

Keywords

  • Functionalization
  • Nanofibers
  • Peptides and proteins
  • Scaffolds
  • Substituents

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