Author, as appears in the article.: Escudero-Casao M, Cardona A, Beltrán-Debón R, Díaz Y, Matheu MI, Castillón S.

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: Flúor Esfingolipidos

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: sergio.castillon@urv.cat raul.beltran@urv.cat maribel.matheu@urv.cat yolanda.diaz@urv.cat

Author identifier: 0000-0002-0690-7549 0000-0001-9691-1906 0000-0001-5216-9260 0000-0001-5567-8108

Last page: 7235

Record's date: 2023-02-18

Journal volume: 16

Papper 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: http://repositori.urv.cat/ca/proteccio-de-dades/

Papper original source: Organic & Biomolecular Chemistry. 16 (39): 7230-7235

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

Article's DOI: 10.1039/c8ob01867g

Entity: Universitat Rovira i Virgili

Journal publication year: 2018

First page: 7230

Publication Type: Journal Publications