Indole-propionic acid derivatives as potent, S1P 3-sparing and EAE efficacious sphingosine-1-phosphate 1 (S1P 1) receptor agonists

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 8, 2012, Pages 2794-2797

  Meng, Qinghua ^a   Zhao, Baowei ^a   Xu, Qiongfeng ^a   Xu, Xuesong ^a   Deng, Guanghui ^a   Li, Chengyong ^a   Luan, Linbo ^a   Ren, Feng ^a   Wang, Hailong ^a   Xu, Heng ^a   Xu, Yan ^a   Zhang, Haibo ^a   Xiang, Jia Ning ^a   Elliott, John D ^a   Guo, Taylor B ^a   Zhao, Yonggang ^a   Zhang, Wei ^a   Lu, Hongtao ^a   Lin, Xichen ^a  

^a GLAXOSMITHKLINE   (China)

Author keywords

Agonist; Experimental autoimmune encephalomyelitis (EAE); Lymphopenia; SAR; Sphingosine 1 phosphate

Indexed keywords

FINGOLIMOD; INDOLEPROPIONIC ACID; RECEPTOR SUBTYPE; SPHINGOSINE 1 PHOSPHATE; SPHINGOSINE 1 PHOSPHATE RECEPTOR;

AGONIST; ALLERGIC ENCEPHALOMYELITIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG CLEARANCE; DRUG EFFICACY; DRUG HALF LIFE; DRUG SELECTIVITY; DRUG SYNTHESIS; LYMPHOCYTE COUNT; LYMPHOCYTOPENIA; MOUSE; NONHUMAN; PERIPHERAL LYMPHOCYTE; STRUCTURE ACTIVITY RELATION;

ANIMALS; DOWN-REGULATION; ENCEPHALOMYELITIS, AUTOIMMUNE, EXPERIMENTAL; INDOLES; LYMPHOCYTES; MICE; MOLECULAR STRUCTURE; PROPIONIC ACIDS; RECEPTORS, LYSOSPHINGOLIPID; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84862778039     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.02.083     Document Type: Article

References (29)

1. For recent reviews on S1P receptors, see: K.P. Cusack, and R.H. Stoffel Curr. Opin. Drug. Discov. Devel. 13 2010 481
2. D. Verzijl, S.L.M. Peters, and A.E. Alewijnse Mol. Cells 29 2010 99
3. H. Rosen, P.J. Gonzalez-Cabrera, M.G. Sanna, and S. Brown Annu. Rev. Biochem. 78 2009 743
4. V. Brinkmann Pharmacol. Ther. 115 2007 84
5. D. Meyer-zu-Heringdorf, and K.H. Jakobs Biochim. Biophys. Acta 1768 2006 923
6. S.E. Gardell, A.E. Dubi, and J. Chun Trends Mol. Med. 12 2006 65
7. V. Brinkmann, A. Billich, T. Baumruker, P. Heining, R. Schmouder, G. Francis, S. Aradhye, and P. Burtin Nature Rev. Drug Discov. 9 2010 883
8. M. Matloubian, C.G. Lo, G. Cinamon, M.J. Lesneski, Y. Xu, V. Brinkmann, M.L. Allende, R.L. Proia, and J.G. Cyster Nature 427 2004 355
9. M.L. Allende, J.L. Dreier, S. Mandala, and R.L. Proia J. Biol. Chem. 279 2004 15396
10. 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, and S. Mandala J. Pharmacol. Exp. Ther. 309 2004 758
11. M.G. Sanna, J. Liao, E. Jo, C. Alfonso, M.-Y. Ahn, M.S. Peterson, B. Webb, S. Lefebvre, J. Chun, N. Gray, and H. Rosen J. Biol. Chem. 279 2004 13839
12. D.J. Buzard, J. Thatte, M. Lerner, J. Edwards, and R.M. Jones Expert Opin. Ther. Patents 18 2008 1141
13. S. Crosignani, A. Bombrun, D. Covini, M. Maio, D. Marin, A. Quattropani, D. Swinnen, D. Simpson, W. Sauer, B. Francon, T. Martin, Y. Cambet, A. Nichols, I. Martinou, F. Burgat-Charvillon, D. Rivron, C. Donini, O. Schott, V. Eligert, L. Novo-Perez, P.-A. Vitte, and J.-F. Arrighi Bioorg. Med. Chem. Lett. 20 2010 1516
14. T. Nishi, S. Miyazaki, T. Takemoto, K. Suzuki, Y. Iio, K. Nakajima, T. Ohnuki, Y. Kawase, F. Nara, S. Inaba, T. Izumi, H. Yuita, K. Oshima, H. Doi, R. Inoue, W. Tomisato, T. Kagari, and T. Shimozato ACS Med. Chem. Lett. 2 2011 368
15. M.H. Bolli, S. Abele, C. Binkert, R. Bravo, S. Buchmann, D. Bur, J. Gatfield, P. Hess, C. Kohl, C. Mangold, B. Mathys, K. Menyhart, C. Muller, O. Nayler, M. Scherz, G. Schmidt, V. Sippel, B. Steiner, D. Strasser, A. Treiber, and T. Weller J. Med. Chem. 53 2010 4198
16. V.J. Cee, M. Frohn, B.A. Lanman, J. Golden, K. Muller, S. Neira, A. Pickrell, H. Arnett, J. Buys, A. Gore, M. Fiorino, M. Horner, A. Itano, M.R. Lee, M. McElvain, S. Middleton, M. Schrag, D. Rivenzon-Segal, H.M. Vargas, H. Xu, Y. Xu, X. Zang, J. Siu, M. Wong, and R.W. Burli ACS Med. Chem. Lett. 2 2011 107
17. E.H. Demont, B.I. Andrews, R.A. Bit, C.A. Campbell, J.W.B. Cooke, N. Deeks, S. Desai, S.J. Dowell, P. Gaskin, J.R.J. Gray, A. Haynes, D.S. Holmes, U. Kumar, M.A. Morse, G.J. Osborne, T. Panchal, B. Patel, A. Perboni, S. Taylor, R. Watson, J. Witherington, and R. Willis ACS Med Chem. Lett. 2 2011 444
18. D. Buzard, S. Han, L. Thoresen, J. Moody, L. Lopez, A. Kawasaki, T. Schrader, C. Sage, Y. Gao, J. Edwards, J. Barden, J. Thatte, L. Fu, M. Solomon, L. Liu, H. Al-Shamma, J. Gatlin, M. Le, C. Xing, S. Espinola, and R.M. Jones Bioorg. Med. Chem. Lett. 21 2011 6013
19. H. Kurata, K. Kusumi, K. Otsuki, R. Suzuki, M. Kurono, Y. Takada, H. Shioya, T. Komiya, H. Mizuno, T. Ono, H. Hagiya, M. Minami, S. Nakade, and H. Habashita Bioorg. Med. Chem. Lett. 21 2011 3885
20. Ahmed, M.; Myatt, J.; Norton, D.; Rivers, D. A. PCT Int. Appl. 2008, WO 2008074821 A1.
21. R.J. Sundberg 1970 The Chemistry of Indoles Academic Press New York
22. G.W. Gribble J. Chem. Soc., Perkin Trans. 1 2000 1045 and references therein.
23. M. Schlosser, A. Ginanneschi, and F. Lerous Eur. J. Org. Chem. 2006 2956
24. S1P1 Tango assay was conducted according to manufacturer's protocol (Catalog K1520, Invitrogen, Carlsbad, CA).
25. S1P3 GeneBLAzer assay was conducted according to manufacturer's protocol (Catalog K1713, Invitrogen, Carlsbad, CA).
26. S. Mandala, R. Hajdu, J. Bergstrom, E. Quackenbush, J. Xie, J. Milligan, R. Thornton, G.J. Shei, D. Card, and C. Keohane Science 296 2002 346
27. M.G. Sanna, J. Liao, E. Jo, C. Alfonso, M.Y. Ahn, M.S. Peterson, B. Webb, S. Lefebvre, J. Chun, and N. Gray J. Biol. Chem. 279 2004 434
28. D. Papadopoulos, J. Rundle, R. Patel, I. Marshall, J. Stretton, R. Eaton, J.C. Richardson, M.I. Gonzalez, K.L. Philpott, and R. Reynolds J. Neurosci. Res. 88 2010 346
29. M. Peiris, G.R. Monteith, S.J. Roberts-Thomson, and P.J. Cabot J. Neurosci. Methods 163 2007 245