Articles producció científicaBioquímica i Biotecnologia

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

  • Identification data

    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.

  • Others:

    Link to the original source: https://pubs.rsc.org/en/content/articlelanding/2018/ob/c8ob01867g#!divAbstract
    APA: Escudero-Casao, Margarita; Cardona, Adria; Beltran-Debon, Raul; Diaz, Yolanda; Isabel Matheu, M; Castillon, Sergio (2018). Fluorinated triazole-containing sphingosine analogues. Syntheses and in vitro evaluation as SPHK inhibitors. ORGANIC & BIOMOLECULAR CHEMISTRY, 16(39), 7230-7235. DOI: 10.1039/c8ob01867g
    Paper original source: ORGANIC & BIOMOLECULAR CHEMISTRY. 16 (39): 7230-7235
    Article's DOI: 10.1039/c8ob01867g
    Journal publication year: 2018-10-21
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/publishedVersion
    Record's date: 2026-05-09
    First page: 7230
    URV's Author/s: Beltrán Debón, Raúl Alejandro / Castillón Miranda, Sergio / Díaz Giménez, María Yolanda / Matheu Malpartida, María Isabel
    Department: Química Analítica i Química Orgànica, Bioquímica i Biotecnologia
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Publication Type: Journal Publications
    Last page: 7235
    ISSN: 14770520
    Author, as appears in the article.: Escudero-Casao, Margarita; Cardona, Adria; Beltran-Debon, Raul; Diaz, Yolanda; Isabel Matheu, M; Castillon, Sergio
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Journal volume: 16
    Thematic Areas: Physical and theoretical chemistry, Organic chemistry, Interdisciplinar, General medicine, Chemistry, organic, Biochemistry, Astronomia / física
    Author's mail: sergio.castillon@urv.cat, sergio.castillon@urv.cat, yolanda.diaz@urv.cat, yolanda.diaz@urv.cat, yolanda.diaz@urv.cat, maribel.matheu@urv.cat, maribel.matheu@urv.cat, raul.beltran@urv.cat, raul.beltran@urv.cat

  • Keywords:

    Triazoles
    Stereoisomerism
    Sphingosine kinase
    Sphingosine
    Phosphotransferases (alcohol group acceptor)
    Halogenation
    Flúor
    Esfingolipidos
    Enzyme inhibitors
    Click chemistry
    Chemistry techniques
    synthetic
    Biochemistry
    Chemistry
    Organic
    Organic Chemistry
    Physical and Theoretical Chemistry
    Interdisciplinar
    General medicine
    Astronomia / física

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