Autor según el artículo: Escudero-Casao, Margarita; Cardona, Adria; Beltran-Debon, Raul; Diaz, Yolanda; Isabel Matheu, M; Castillon, Sergio
Departamento: Química Analítica i Química Orgànica; Bioquímica i Biotecnologia
Autor/es de la URV: Beltrán Debón, Raúl Alejandro / Castillón Miranda, Sergio / Díaz Giménez, María Yolanda / Matheu Malpartida, María Isabel
Palabras clave: Triazoles; Stereoisomerism; Sphingosine kinase; Sphingosine; Phosphotransferases (alcohol group acceptor); Halogenation; Flúor; Esfingolipidos; Enzyme inhibitors; Click chemistry; Chemistry techniques, synthetic
Resumen: 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.
Áreas temáticas: 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
Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
ISSN: 14770520
Direcció de correo del autor: yolanda.diaz@urv.cat; maribel.matheu@urv.cat; raul.beltran@urv.cat; sergio.castillon@urv.cat
Página final: 7235
Fecha de alta del registro: 2025-01-08
Volumen de revista: 16
Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
Enlace a la fuente original: https://pubs.rsc.org/en/content/articlelanding/2018/ob/c8ob01867g#!divAbstract
URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
Referencia al articulo segun fuente origial: Organic & Biomolecular Chemistry. 16 (39): 7230-7235
Referencia de l'ítem segons les normes 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
DOI del artículo: 10.1039/c8ob01867g
Entidad: Universitat Rovira i Virgili
Año de publicación de la revista: 2018
Página inicial: 7230
Tipo de publicación: Journal Publications
Repositori URV