Fluorinated triazole-containing sphingosine analogues. Syntheses and in vitro evaluation as SPHK inhibitors

Identifier:  imarina:5133170

Handle: https://hdl.handle.net/20.500.11797/imarina5133170

Authors:  Escudero-Casao, Margarita; Cardona, Adria; Beltran-Debon, Raul; Diaz, Yolanda; Isabel Matheu, M; Castillon, Sergio

Abstract:
Sphingosine analogues with a rigid triazole moiety in the aliphatic chain and systematic modifications in the polar head and different degrees of fluorination at the terminus of the alkylic chain were synthesized from a common alkynyl aziridine key synthon. This key synthon was obtained by enantioselective organocatalyzed aziridination and it was subsequently ring opened in a regioselective manner in acidic medium. Up to 16 sphingosine analogues were prepared in a straightforward manner. The in vitro activity of the obtained products as SPHK1 and SPHK2 inhibitors was evaluated, displaying comparable activity to that of DMS.