New fluorinated agonists for targeting the sphingosin-1-phosphate receptor 1 (S1P1). Issue 22 (15th November 2015)

• Record Type: Journal Article
• Authors: Shaikh, Rizwan S.; Keul, Petra; Schäfers, Michael; Levkau, Bodo; Haufe, Günter
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 25:Issue 22(2015)
• Page Start: 5048
• Page End: 5051
• Publication Date: 2015-11-15
• Subjects: Fluorine -- FTY720 analogues -- G protein-coupled receptors -- Sphingosine-1-phosphate (S1P) -- S1P1 receptor agonist; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2015.10.026
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: The sphingosine-1-phosphate receptor type 1 (S1P1 ) is involved in fundamental biological processes such as regulation of immune cell trafficking, vascular barrier function and angiogenesis. This Letter presents multistep syntheses of various fluorine substituted 12-aryl analogues of the drug fingolimod (FTY720) and a seven-steps route to 2-amino-17, 17-difluoro-2-(hydroxymethyl)heptadecan-1-ol. In vitro and in vivo tests proved all these compounds as potent S1P1 receptor agonists.