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1
Chiral vinylphosphonate and phosphonate analogues of the immunosuppressive agent FTY720.免疫抑制剂FTY720的手性乙烯基膦酸酯及膦酸酯类似物。
J Org Chem. 2009 Apr 17;74(8):3192-5. doi: 10.1021/jo900023u.
2
(S)-FTY720-vinylphosphonate, an analogue of the immunosuppressive agent FTY720, is a pan-antagonist of sphingosine 1-phosphate GPCR signaling and inhibits autotaxin activity.(S)-FTY720-乙烯膦酸酯是免疫抑制剂 FTY720 的类似物，是鞘氨醇 1-磷酸 GPCR 信号的泛拮抗剂，并抑制自分泌运动因子（ATX）活性。
Cell Signal. 2010 Oct;22(10):1543-53. doi: 10.1016/j.cellsig.2010.05.023. Epub 2010 Jun 4.
3
FTY720 and (S)-FTY720 vinylphosphonate inhibit sphingosine kinase 1 and promote its proteasomal degradation in human pulmonary artery smooth muscle, breast cancer and androgen-independent prostate cancer cells.FTY720 和（S）-FTY720 乙烯膦酸酯抑制人肺动脉平滑肌细胞、乳腺癌和雄激素非依赖性前列腺癌细胞中的鞘氨醇激酶 1 并促进其蛋白酶体降解。
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4
Synthesis and biological evaluation of sphingosine kinase substrates as sphingosine-1-phosphate receptor prodrugs.作为1-磷酸鞘氨醇受体前药的鞘氨醇激酶底物的合成与生物学评价。
Bioorg Med Chem. 2009 Aug 15;17(16):6123-36. doi: 10.1016/j.bmc.2009.04.015. Epub 2009 Apr 12.
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Synthesis of 4(5)-phenylimidazole-based analogues of sphingosine-1-phosphate and FTY720: discovery of potent S1P1 receptor agonists.基于4(5)-苯基咪唑的鞘氨醇-1-磷酸酯类似物和FTY720的合成：强效S1P1受体激动剂的发现
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6
Asymmetric synthesis of conformationally constrained fingolimod analogues--discovery of an orally active sphingosine 1-phosphate receptor type-1 agonist and receptor type-3 antagonist.构象受限的芬戈莫德类似物的不对称合成——一种口服活性的1-磷酸鞘氨醇受体1型激动剂和受体3型拮抗剂的发现
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7
Functional characterization of sphingosine 1-phosphate receptor agonist in human endothelial cells.1-磷酸鞘氨醇受体激动剂在人内皮细胞中的功能特性研究
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8
FTY720 (s)-phosphonate preserves sphingosine 1-phosphate receptor 1 expression and exhibits superior barrier protection to FTY720 in acute lung injury.FTY720（S）-膦酸盐可维持鞘氨醇 1-磷酸受体 1 的表达，并在急性肺损伤中表现出优于 FTY720 的屏障保护作用。
Crit Care Med. 2014 Mar;42(3):e189-99. doi: 10.1097/CCM.0000000000000097.
9
Asymmetric synthesis and biological evaluation of the enantiomeric isomers of the immunosuppressive FTY720-phosphate.免疫抑制性磷酸化FTY720对映体异构体的不对称合成及生物学评价
Bioorg Med Chem. 2005 Jan 17;13(2):425-32. doi: 10.1016/j.bmc.2004.10.008.
10
FTY720 analogues as sphingosine kinase 1 inhibitors: enzyme inhibition kinetics, allosterism, proteasomal degradation, and actin rearrangement in MCF-7 breast cancer cells.FTY720 类似物作为鞘氨醇激酶 1 抑制剂：MCF-7 乳腺癌细胞中的酶抑制动力学、别构调节、蛋白酶体降解和肌动蛋白重排。
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Markovnikov-addition of H-phosphonates to terminal alkynes under metal- and solvent-free conditions.在无金属和无溶剂条件下，H-膦酸酯与末端炔烃的马氏加成反应。
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Pharmacological sphingosine-1 phosphate receptor 1 targeting in cigarette smoke-induced emphysema in mice.药物靶向鞘氨醇-1-磷酸受体 1 治疗香烟烟雾诱导的小鼠肺气肿。
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MRSA-induced endothelial permeability and acute lung injury are attenuated by FTY720 S-phosphonate.FTY720 S-膦酸盐可减轻耐甲氧西林金黄色葡萄球菌诱导的内皮通透性和急性肺损伤。
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6
Sphingosine-1-phosphate receptor-independent lung endothelial cell barrier disruption induced by FTY720 regioisomers.FTY720区域异构体诱导的不依赖于鞘氨醇-1-磷酸受体的肺内皮细胞屏障破坏
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Sphingosine 1-Phosphate Activation of EGFR As a Novel Target for Meningitic Escherichia coli Penetration of the Blood-Brain Barrier.1-磷酸鞘氨醇激活表皮生长因子受体作为脑膜炎性大肠杆菌穿越血脑屏障的新靶点
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本文引用的文献

1
Camptothecins: a SAR/QSAR study.喜树碱类：一项构效关系/定量构效关系研究。
Chem Rev. 2009 Jan;109(1):213-35. doi: 10.1021/cr0780210.
2
Prompt determination of absolute configuration for epoxy alcohols via exciton chirality protocol.通过激子手性法快速确定环氧醇的绝对构型。
J Am Chem Soc. 2008 Dec 3;130(48):16126-7. doi: 10.1021/ja805058t.
3
Production and release of sphingosine 1-phosphate and the phosphorylated form of the immunomodulator FTY720.鞘氨醇-1-磷酸及免疫调节剂FTY720磷酸化形式的产生与释放。
Biochim Biophys Acta. 2008 Sep;1781(9):496-502. doi: 10.1016/j.bbalip.2008.05.003. Epub 2008 Jun 13.
4
Synthesis of the key intermediate, diethyl 2-acetylamino-2-(2-(4-octanoylphenyl)ethyl)propane-1,3-dioate, of the immunomodulatory agent FTY720 (fingolimod).
Chem Pharm Bull (Tokyo). 2008 Apr;56(4):595-7. doi: 10.1248/cpb.56.595.
5
The immunomodulator FTY720 has a direct cytoprotective effect in oligodendrocyte progenitors.免疫调节剂FTY720对少突胶质前体细胞具有直接的细胞保护作用。
J Pharmacol Exp Ther. 2007 Nov;323(2):626-35. doi: 10.1124/jpet.107.123927. Epub 2007 Aug 28.
6
FTY720: a most promising immunosuppressant modulating immune cell functions.FTY720：一种极具潜力的调节免疫细胞功能的免疫抑制剂。
Mini Rev Med Chem. 2007 Aug;7(8):845-50. doi: 10.2174/138955707781387948.
7
Current perspectives on FTY720.
Expert Opin Investig Drugs. 2007 Apr;16(4):505-18. doi: 10.1517/13543784.16.4.505.
8
FTY720, an immunomodulatory sphingolipid mimetic: translation of a novel mechanism into clinical benefit in multiple sclerosis.FTY720，一种免疫调节性鞘脂类似物：将一种新机制转化为多发性硬化症的临床益处。
Expert Opin Investig Drugs. 2007 Mar;16(3):283-9. doi: 10.1517/13543784.16.3.283.
9
Immunosuppressive and anti-angiogenic sphingosine 1-phosphate receptor-1 agonists induce ubiquitinylation and proteasomal degradation of the receptor.免疫抑制和抗血管生成的1-磷酸鞘氨醇受体-1激动剂可诱导该受体的泛素化和蛋白酶体降解。
J Biol Chem. 2007 Mar 23;282(12):9082-9. doi: 10.1074/jbc.M610318200. Epub 2007 Jan 21.
10
Mapping pathways downstream of sphingosine 1-phosphate subtype 1 by differential chemical perturbation and proteomics.通过差异化学扰动和蛋白质组学绘制1-磷酸鞘氨醇1型下游的信号通路
J Biol Chem. 2007 Mar 9;282(10):7254-64. doi: 10.1074/jbc.M610581200. Epub 2007 Jan 10.

免疫抑制剂FTY720的手性乙烯基膦酸酯及膦酸酯类似物。

Chiral vinylphosphonate and phosphonate analogues of the immunosuppressive agent FTY720.

作者信息

Lu Xuequan, Sun Chaode, Valentine William J, Shuyu E, Liu Jianxiong, Tigyi Gabor, Bittman Robert

机构信息

Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, New York 11367-1597, USA.

出版信息

J Org Chem. 2009 Apr 17;74(8):3192-5. doi: 10.1021/jo900023u.

DOI:10.1021/jo900023u
PMID:19296586
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2747615/
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.

摘要

描述了FTY720手性等排膦酸酯类似物的首次对映选择性合成。这些类似物之一，FTY720-(E)-乙烯基膦酸酯(S)-5，而非其R对映体，在肠上皮细胞中引发了强大的抗凋亡作用，表明它通过对受体的对映选择性激活发挥作用。(S)-5未能激活1型鞘氨醇-1-磷酸(S1P(1))受体。