Articles producció científica> Química Analítica i Química Orgànica

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

  • Dades identificatives

    Identificador: imarina:5133170
    Autors:
    Escudero-Casao M, Cardona A, Beltrán-Debón R, Díaz Y, Matheu MI, Castillón S.
    Resum:
    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.
  • Altres:

    Autor segons l'article: Escudero-Casao M, Cardona A, Beltrán-Debón R, Díaz Y, Matheu MI, Castillón S.
    Departament: Química Analítica i Química Orgànica Bioquímica i Biotecnologia
    Autor/s de la URV: Beltrán Debón, Raúl Alejandro / Castillón Miranda, Sergio / Díaz Giménez, María Yolanda / Matheu Malpartida, María Isabel
    Paraules clau: Flúor Esfingolipidos
    Resum: 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.
    Àrees temàtiques: Química Physical and theoretical chemistry Organic chemistry Odontología Medicina ii Medicina i Materiais Interdisciplinar General medicine Farmacia Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, organic Biotecnología Biodiversidade Biochemistry
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 14770520
    Adreça de correu electrònic de l'autor: yolanda.diaz@urv.cat maribel.matheu@urv.cat raul.beltran@urv.cat sergio.castillon@urv.cat
    Identificador de l'autor: 0000-0001-5567-8108 0000-0001-5216-9260 0000-0001-9691-1906 0000-0002-0690-7549
    Pàgina final: 7235
    Data d'alta del registre: 2024-09-07
    Volum de revista: 16
    Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
    Enllaç font original: https://pubs.rsc.org/en/content/articlelanding/2018/ob/c8ob01867g#!divAbstract
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: Organic & Biomolecular Chemistry. 16 (39): 7230-7235
    Referència de l'ítem segons les normes APA: Escudero-Casao M, Cardona A, Beltrán-Debón R, Díaz Y, Matheu MI, Castillón S. (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
    DOI de l'article: 10.1039/c8ob01867g
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2018
    Pàgina inicial: 7230
    Tipus de publicació: Journal Publications
  • Paraules clau:

    Biochemistry,Chemistry, Organic,Organic Chemistry,Physical and Theoretical Chemistry
    Flúor
    Esfingolipidos
    Química
    Physical and theoretical chemistry
    Organic chemistry
    Odontología
    Medicina ii
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    Farmacia
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Chemistry, organic
    Biotecnología
    Biodiversidade
    Biochemistry
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