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Issue 39, 2018
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Fluorinated triazole-containing sphingosine analogues. Syntheses and in vitro evaluation as SPHK inhibitors

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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.

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

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Publication details

The article was received on 01 Aug 2018, accepted on 18 Sep 2018 and first published on 24 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB01867G
Citation: Org. Biomol. Chem., 2018,16, 7230-7235
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    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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