Chiral vinylphosphonate and phosphonate analogues of the immunosuppressive agent FTY720

  • J Org Chem. 2009 Apr 17;74(8):3192-5. doi: 10.1021/jo900023u.
Xuequan Lu  1 ,  Chaode Sun ,  William J Valentine ,  E Shuyu ,  Jianxiong Liu ,  Gabor Tigyi ,  Robert Bittman
Affiliations
  • 1. Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, New York 11367-1597, USA.
PMID: 19296586 DOI: 10.1021/jo900023u
Abstract

The first enantioselective synthesis of chiral isosteric phosphonate analogues of FTY720 is described. One of these analogues, FTY720-(E)-vinylphosphonate (S)-5, but not its R enantiomer, elicited a potent antiapoptotic effect in intestinal epithelial cells, suggesting that it exerts its action via the enantioselective activation of a receptor. (S)-5 failed to activate the sphingosine 1-phosphate type 1 (S1P(1)) receptor.

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