Literature DB >> 20188554

Stereochemistry-activity relationship of orally active tetralin S1P agonist prodrugs.

Bin Ma1, Kevin M Guckian, Edward Yin-Shiang Lin, Wen-Cherng Lee, Daniel Scott, Gnanasambandam Kumaravel, Timothy L Macdonald, Kevin R Lynch, Cheryl Black, Sowmya Chollate, Kyungmin Hahm, Gregg Hetu, Ping Jin, Yi Luo, Ellen Rohde, Anthony Rossomando, Robert Scannevin, Joy Wang, Chunhua Yang.   

Abstract

Modifying FTY720, an immunosuppressant modulator, led to a new series of well phosphorylated tetralin analogs as potent S1P1 receptor agonists. The stereochemistry effect of tetralin ring was probed, and (-)-(R)-2-amino-2-((S)-6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)propan-1-ol was identified as a good SphK2 substrate and potent S1P1 agonist with good oral bioavailability. 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID： 20188554      PMCID： PMC2843818          DOI： 10.1016/j.bmcl.2010.02.006

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  13 in total

1.  Alteration of lymphocyte trafficking by sphingosine-1-phosphate receptor agonists.

Authors:  Suzanne Mandala; Richard Hajdu; James Bergstrom; Elizabeth Quackenbush; Jenny Xie; James Milligan; Rosemary Thornton; Gan-Ju Shei; Deborah Card; CarolAnn Keohane; Mark Rosenbach; Jeffrey Hale; Christopher L Lynch; Kathleen Rupprecht; William Parsons; Hugh Rosen
Journal:  Science       Date:  2002-03-28       Impact factor: 47.728

2.  The immune modulator FTY720 targets sphingosine 1-phosphate receptors.

Authors:  Volker Brinkmann; Michael D Davis; Christopher E Heise; Rainer Albert; Sylvain Cottens; Robert Hof; Christian Bruns; Eva Prieschl; Thomas Baumruker; Peter Hiestand; Carolyn A Foster; Markus Zollinger; Kevin R Lynch
Journal:  J Biol Chem       Date:  2002-04-19       Impact factor: 5.157

3.  Oral fingolimod (FTY720) for relapsing multiple sclerosis.

Authors:  Ludwig Kappos; Jack Antel; Giancarlo Comi; Xavier Montalban; Paul O'Connor; Chris H Polman; Tomas Haas; Alexander A Korn; Goeril Karlsson; Ernst W Radue
Journal:  N Engl J Med       Date:  2006-09-14       Impact factor: 91.245

4.  Novel immunomodulator FTY720 is phosphorylated in rats and humans to form a single stereoisomer. Identification, chemical proof, and biological characterization of the biologically active species and its enantiomer.

Authors:  Rainer Albert; Klaus Hinterding; Volker Brinkmann; Danilo Guerini; Constanze Müller-Hartwieg; Helmut Knecht; Corinne Simeon; Markus Streiff; Trixie Wagner; Karl Welzenbach; Frédéric Zécri; Markus Zollinger; Nigel Cooke; Eric Francotte
Journal:  J Med Chem       Date:  2005-08-11       Impact factor: 7.446

5.  S1P3 receptor-induced reorganization of epithelial tight junctions compromises lung barrier integrity and is potentiated by TNF.

Authors:  Yasuhiro Gon; Malcolm R Wood; William B Kiosses; Euijung Jo; M Germana Sanna; Jerold Chun; Hugh Rosen
Journal:  Proc Natl Acad Sci U S A       Date:  2005-06-20       Impact factor: 11.205

Review 6.  Signaling and biological actions of sphingosine 1-phosphate.

Authors:  Timothy Hla
Journal:  Pharmacol Res       Date:  2003-05       Impact factor: 7.658

7.  Synthesis and immunosuppressive activity of 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols.

Authors:  M Kiuchi; K Adachi; T Kohara; M Minoguchi; T Hanano; Y Aoki; T Mishina; M Arita; N Nakao; M Ohtsuki; Y Hoshino; K Teshima; K Chiba; S Sasaki; T Fujita
Journal:  J Med Chem       Date:  2000-07-27       Impact factor: 7.446

8.  Amelioration of experimental autoimmune encephalomyelitis in Lewis rats by FTY720 treatment.

Authors:  Masayuki Fujino; Naoko Funeshima; Yusuke Kitazawa; Hiromitsu Kimura; Hiroshi Amemiya; Seiichi Suzuki; Xiao-Kang Li
Journal:  J Pharmacol Exp Ther       Date:  2003-04       Impact factor: 4.030

9.  Immune cell regulation and cardiovascular effects of sphingosine 1-phosphate receptor agonists in rodents are mediated via distinct receptor subtypes.

Authors:  M Forrest; S-Y Sun; R Hajdu; J Bergstrom; D Card; G Doherty; J Hale; C Keohane; C Meyers; J Milligan; S Mills; N Nomura; H Rosen; M Rosenbach; G-J Shei; I I Singer; M Tian; S West; V White; J Xie; R L Proia; S Mandala
Journal:  J Pharmacol Exp Ther       Date:  2004-01-27       Impact factor: 4.030

Review 10.  Chemical modulators of sphingosine-1-phosphate receptors as barrier-oriented therapeutic molecules.

Authors:  David Marsolais; Hugh Rosen
Journal:  Nat Rev Drug Discov       Date:  2009-03-20       Impact factor: 84.694
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  4 in total

1.  Biosynthesis of alkyl lysophosphatidic acid by diacylglycerol kinases.

Authors:  Amanda M Gellett; Yugesh Kharel; Manjula Sunkara; Andrew J Morris; Kevin R Lynch
Journal:  Biochem Biophys Res Commun       Date:  2012-05-22       Impact factor: 3.575

2.  Novel Potent Selective Orally Active S1P5 Receptor Antagonists.

Authors:  Bin Ma; Kevin M Guckian; Xiao-Gao Liu; Chunhua Yang; Bing Li; Robert Scannevin; Michaël Mingueneau; Annabelle Drouillard; Thierry Walzer
Journal:  ACS Med Chem Lett       Date:  2021-01-15       Impact factor: 4.345

3.  Role of S1P/S1PR3 axis in release of CCL20 from human bronchial epithelial cells.

Authors:  Yoshitaka Kawa; Tatsuya Nagano; Asuka Yoshizaki; Ryota Dokuni; Masahiro Katsurada; Tomomi Terashita; Yuichiro Yasuda; Kanoko Umezawa; Masatsugu Yamamoto; Hiroshi Kamiryo; Kazuyuki Kobayashi; Yoshihiro Nishimura
Journal:  PLoS One       Date:  2018-09-07       Impact factor: 3.240

4.  Discovery of Potent Selective Nonzinc Binding Autotaxin Inhibitor BIO-32546.

Authors:  Bin Ma; Lei Zhang; Lihong Sun; Zhili Xin; Gnanasambandam Kumaravel; Douglas Marcotte; Jayanth V Chodaparambil; Qin Wang; Angela Wehr; Jing Jing; Victor Sukbong Hong; Ti Wang; Carol Huang; Zhaohui Shao; Sha Mi
Journal:  ACS Med Chem Lett       Date:  2021-06-14       Impact factor: 4.632
  4 in total

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