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.
Original language | English |
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Pages (from-to) | 1660-1664 |
Journal | European Journal of Organic Chemistry |
Volume | 2016 |
DOIs | |
Publication status | Published - 2016 |
Keywords
- Amyloid beta-peptides
- Diagnostic agents
- Domino reactions
- Fluorescence
- Medicinal chemistry
- Organocatalysis
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry