Chiral Vinylphosphonate and Phosphonate Analogues of the Immunosuppressive Agent FTY720

被引：44

作者：

Lu, Xuequan ^{[1
]}

Sun, Chaode ^{[1
]}

Valentine, William J. ^{[2
]}

Shuyu, E. ^{[2
]}

Liu, Jianxiong ^{[2
]}

Tigyi, Gabor ^{[2
]}

Bittmani, Robert ^{[1
]}

机构：

[1] CUNY Queens Coll, Dept Chem & Biochem, Flushing, NY 11367 USA

[2] Univ Tennessee, Ctr Hlth Sci, Dept Physiol, Memphis, TN 38163 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 08期

关键词：

IMMUNE MODULATOR FTY720; SPHINGOSINE; 1-PHOSPHATE; IMMUNOMODULATOR FTY720; RECEPTOR AGONISTS; OLIGODENDROCYTE PROGENITORS; MULTIPLE-SCLEROSIS; PHOSPHATE-ESTERS; SPHINGOSINE-1-PHOSPHATE; FINGOLIMOD; FORM;

D O I：

10.1021/jo900023u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3192 / 3195

页数：4

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