Fluorinated triazole-containing sphingosine analogues. Syntheses and in vitro evaluation as SPHK inhibitorsElectronic supplementary information (ESI) available: Experimental details, NMR spectra and additional graphics. See DOI: 10.1039/c8ob01867g

• Main Authors: Escudero-Casao, Margarita, Cardona, Adrià, Beltrán-Debón, Raúl, Díaz, Yolanda, Matheu, M. Isabel, Castillón, Sergio
• Format: Journal Article
• Language: English
• Published: 10.10.2018
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c8ob01867g

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. Fluorinated triazole-containing sphingosine analogues as SPHK inhibitors were synthesized from a common alkynyl aziridine key synthon via enantioselective organocatalyzed aziridination.