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- Title
A Versatile Approach to CF<sub>3</sub>-Containing 2-Pyrrolidones by Tandem Michael Addition-Cyclization: Exemplification in the Synthesis of Amidine Class BACE1 Inhibitors.
- Authors
Mateu, Natalia; Ciordia, Myriam; Delgado, Oscar; Sánchez ‐ Roselló, María; Trabanco, Andrés A.; Van Gool, Michiel; Tresadern, Gary; Pérez ‐ Benito, Laura; Fustero, Santos
- Abstract
The synthesis of new fluorinated pyrrolidones starting from unprotected amino esters and amino nitriles through a Michael addition-lactamization sequence is described. The resulting CF3-containing building blocks, bearing a quaternary stereogenic center adjacent to the fluorinated group, have been converted into amino pyrrolidines that display potent β-secretase 1 (BACE1) inhibitory activity. This work constitutes an example of selective fluorination as a valid strategy for the modulation of physicochemical and biological properties of lead compounds in drug discovery.
- Subjects
MICHAEL reaction; AMIDINES; RING formation (Chemistry); ALZHEIMER'S disease; COGNITIVE ability; FLUORINATION; LEAD compounds
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 33, p11719
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201501662