A Versatile Approach to CF3-Containing 2-Pyrrolidones by Tandem Michael Addition-Cyclization: Exemplification in the Synthesis of Amidine Class BACE1 Inhibitors

Autor: N. MATEU, M. CIORDIA, O. DELGADO, M. SANCHEZ, A. TRABANCO, M. VAN GOOL, G. TRESADERN, L. PEREZ-BENITO, S. FUSTERO
Rok vydání: 2015
Předmět:
Zdroj: CHEMISTRY-A EUROPEAN JOURNAL
r-CIPF: Repositorio Institucional Producción Científica del Centro de Investigación Principe Felipe (CIPF)
Centro de Investigación Principe Felipe (CIPF)
r-CIPF. Repositorio Institucional Producción Científica del Centro de Investigación Principe Felipe (CIPF)
instname
ISSN: 0947-6539
Popis: 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 -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.
Databáze: OpenAIRE
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