Author, as appears in the article.: Escudero-Casao, Margarita; Cardona, Adria; Beltran-Debon, Raul; Diaz, Yolanda; Isabel Matheu, M; Castillon, Sergio
Department: Química Analítica i Química Orgànica; Bioquímica i Biotecnologia
URV's Author/s: Beltrán Debón, Raúl Alejandro / Castillón Miranda, Sergio / Díaz Giménez, María Yolanda / Matheu Malpartida, María Isabel
Keywords: Triazoles; Stereoisomerism; Sphingosine kinase; Sphingosine; Phosphotransferases (alcohol group acceptor); Halogenation; Flúor; Esfingolipidos; Enzyme inhibitors; Click chemistry; Chemistry techniques, synthetic
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.
Thematic Areas: 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
licence for use: https://creativecommons.org/licenses/by/3.0/es/
ISSN: 14770520
Author's mail: yolanda.diaz@urv.cat; maribel.matheu@urv.cat; raul.beltran@urv.cat; sergio.castillon@urv.cat
Last page: 7235
Record's date: 2025-01-08
Journal volume: 16
Paper version: info:eu-repo/semantics/publishedVersion
Link to the original source: https://pubs.rsc.org/en/content/articlelanding/2018/ob/c8ob01867g#!divAbstract
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Paper original source: Organic & Biomolecular Chemistry. 16 (39): 7230-7235
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
Article's DOI: 10.1039/c8ob01867g
Entity: Universitat Rovira i Virgili
Journal publication year: 2018
First page: 7230
Publication Type: Journal Publications
Repositori URV