Synthesis of fluorinated agonist of sphingosine-1-phosphate receptor 1

[Display omitted] The bioactive metabolite sphingosine-1-phosphate (S1P), a product of sphingosine kinases (SphKs), mediates diverse biological processes such as cell differentiation, proliferation, survival and angiogenesis. A fluorinated analogue of S1P receptor agonist has been synthesized by uti...

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Veröffentlicht in:	Bioorganic & medicinal chemistry 2014-09, Vol.22 (17), p.4955-4960
Hauptverfasser:	Aliouane, Lucie, Chao, Sovy, Brizuela, Leyre, Pfund, Emmanuel, Cuvillier, Olivier, Jean, Ludovic, Renard, Pierre-Yves, Lequeux, Thierry
Format:	Artikel
Sprache:	eng
Schlagworte:	Agonist Cell Line, Tumor Cell Proliferation - drug effects Cell Survival - drug effects Chemical Sciences Difluorophosphonate Dose-Response Relationship, Drug Fluorine Halogenation Humans Male Molecular Structure Organic chemistry Organophosphates - chemical synthesis Organophosphates - chemistry Organophosphates - pharmacology Receptors, Lysosphingolipid - agonists Sphingosine - analogs & derivatives Sphingosine - chemical synthesis Sphingosine - chemistry Sphingosine - pharmacology Sphingosine-1-phosphate Structure-Activity Relationship
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Zusammenfassung:	[Display omitted] The bioactive metabolite sphingosine-1-phosphate (S1P), a product of sphingosine kinases (SphKs), mediates diverse biological processes such as cell differentiation, proliferation, survival and angiogenesis. A fluorinated analogue of S1P receptor agonist has been synthesized by utilizing a ring opening reaction of oxacycles by a lithiated difluoromethylphosphonate anion as the key reaction. In vitro activity of this S1P analogue is also reported.
ISSN:	0968-0896 1464-3391
DOI:	10.1016/j.bmc.2014.06.038