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- Title
Synthesis and Preliminary Biological Evaluation of Fluorescent Glycofused Tricyclic Derivatives of Amyloid β-Peptide Ligands.
- Authors
D'Orazio, Giuseppe; Colombo, Laura; Salmona, Mario; La Ferla, Barbara
- Abstract
Fluorescent glycofused tricyclic compounds were synthesized through the domino conjugate oxa-Michael addition/aldol condensation of 2-hydroxybenzaldehydes with protected 3-oxoglucal by exploiting activation with an organocatalyst. Stereoselectivity was obtained by using ( R)-(+)-α,α-diphenyl-2-pyrrolidinemethanol trimethylsilyl ether as the catalyst. All synthesized compounds presented good optical properties. All compounds were able to bind to synthetic amyloid β 1-42 peptide aggregates and to label amyloid plaques from brain sections of transgenic mice affected with Alzheimer's disease with staining properties comparable to thioflavin T.
- Subjects
AMYLOID; MICHAEL reaction; ALDOL condensation; CHEMICAL synthesis; BENZALDEHYDE; TRIMETHYLSILYL compounds
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 9, p1660
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201501593