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

Literature Information

Publication Date 2018-09-24
DOI 10.1039/C8OB01867G
Impact Factor 3.876
Authors

Margarita Escudero-Casao, Adrià Cardona, Raúl Beltrán-Debón, Yolanda Díaz, M. Isabel Matheu, Sergio Castillón


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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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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