Intramolecular Povarov Reactions for the Synthesis of Chromenopyridine Fused 2-Pyridone Polyheterocycles Binding to α-Synuclein and Amyloid-β Fibrils | Zendy

Dan E. Adolfsson | Zendy; Mohit Tyagi | Zendy; Pardeep Singh | Zendy; Adrian Deuschmann | Zendy; Jörgen Ådén | Zendy; Anna L. Gharibyan | Zendy; Sanduni Wasana Jayaweera | Zendy; Anders E. G. Lindgren | Zendy; Anders Olofsson | Zendy; Fredrik Almqvist | Zendy

Open Access

Intramolecular Povarov Reactions for the Synthesis of Chromenopyridine Fused 2-Pyridone Polyheterocycles Binding to α-Synuclein and Amyloid-β Fibrils

Author(s) -

Dan E. Adolfsson,

Mohit Tyagi,

Pardeep Singh,

Adrian Deuschmann,

Jörgen Ådén,

Anna L. Gharibyan,

Sanduni Wasana Jayaweera,

Anders E. G. Lindgren,

Anders Olofsson,

Fredrik Almqvist

Publication year - 2020

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.0c01699

Subject(s) - intramolecular force , chemistry , peptidomimetic , amyloid fibril , nitro , fibril , in vitro , amyloid β , alkylation , combinatorial chemistry , amyloid (mycology) , stereochemistry , folding (dsp implementation) , catalysis , biochemistry , peptide , organic chemistry , medicine , inorganic chemistry , alkyl , disease , pathology , electrical engineering , engineering

A BF 3 ·OEt 2 catalyzed intramolecular Povarov reaction was used to synthesize 15 chromenopyridine fused thiazolino-2-pyridone peptidomimetics. The reaction works with several O -alkylated salicylaldehydes and amino functionalized thiazolino-2-pyridones, to generate polyheterocycles with diverse substitution. The synthesized compounds were screened for their ability to bind α-synuclein and amyloid β fibrils in vitro . Analogues substituted with a nitro group bind to mature amyloid fibrils, and the activity moreover depends on the positioning of this functional group.

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