Issue 39, 2018

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
01 Aug 2018
Accepted
18 Sep 2018
First published
24 Sep 2018
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2018,16, 7230-7235

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

M. Escudero-Casao, A. Cardona, R. Beltrán-Debón, Y. Díaz, M. I. Matheu and S. Castillón, Org. Biomol. Chem., 2018, 16, 7230 DOI: 10.1039/C8OB01867G

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