Structure-activity relationship studies of S1P agonists with a dihydronaphthalene scaffold

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 1, 2012, Pages 144-148

  Kurata, Haruto ^a   Kusumi, Kensuke ^a   Otsuki, Kazuhiro ^a   Suzuki, Ryo ^a   Kurono, Masakuni ^a   Tokuda, Natsuko ^a   Takada, Yuka ^a   Shioya, Hiroki ^a   Mizuno, Hirotaka ^a   Komiya, Takaki ^a   Ono, Takeji ^a   Hagiya, Hiroshi ^a   Minami, Masashi ^a   Nakade, Shinji ^a   Habashita, Hiromu ^a  

^a ONO PHARMACEUTICAL CO   (Japan)

Author keywords

Dihydronaphthalene; Immunomodulator; S1P agonist

Indexed keywords

BENZENE; CHLORINE; METHYL GROUP; NAFOXIDINE; PROPYLENE; SCAFFOLD PROTEIN; SPHINGOSINE 1 PHOSPHATE RECEPTOR;

ARTICLE; DRUG BIOAVAILABILITY; DRUG SELECTIVITY; IN VITRO STUDY; IN VIVO STUDY; LIPOPHILICITY; MOUSE; NONHUMAN; PERIPHERAL LYMPHOCYTE; STRUCTURE ACTIVITY RELATION;

MUS;

EID: 84655176416     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.11.048     Document Type: Article

References (21)

1. M.-J. Lee, S. Thangada, K.P. Claffey, N. Ancellin, C.H. Liu, M. Kluk, M. Volpi, R.I. Sha'afi, and T. Hla Cell 99 1999 301
2. O. Cuvillier, G. Pirianov, B. Kleuser, P.G. Vanek, O.A. Coso, J.S. Gutkind, and S. Spiegel Nature 381 1996 800
3. D. Marsolais, and H. Rosen Nat. Rev. Drug Disc. 8 2009 297
4. T. Fujita, R. Hirose, M. Yoneta, S. Sasaki, K. Inoue, M. Kiuchi, S. Hirase, K. Chiba, H. Sakamoto, and M. Arita J. Med. Chem. 39 1996 4451
5. V. Brinkmann, M.D. Davis, C.E. Heise, R. Albert, S. Cottens, R. Hof, C. Bruns, E. Prieschl, T. Baumruker, P. Hiestand, C.A. Foster, M. Zollinger, and K.R. Lynch J. Biol. Chem. 277 2002 21453
6. V. Brinkmann, A. Billich, T. Baumruker, P. Heining, R. Schmouder, G. Francis, S. Aradhye, and P. Burtin Nat. Rev. Drug Disc. 9 2010 883
7. M. Matloubian, C.G. Lo, G. Cinamon, M.J. Lesneski, Y. Xu, V. Brinkmann, M.L. Allende, R.L. Prola, and J.G. Cyster Nature 427 2004 355
8. 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
9. H.M. Himmel, D.M.Z. Heringdorf, E. Graf, D. Dobrev, A. Kortner, S. Schüler, K.H. Jakobs, and U. Ravens Mol. Pharmacol. 58 2000 449
10. L. Koyrakh, M.I. Roman, V. Brinkmann, and K. Wickman Am. J. Transplant. 5 2005 529
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. M. Hamada, M. Nakamura, M. Kiuchi, K. Marukawa, A. Tomatsu, K. Shimano, N. Sato, K. Sugahara, M. Asayama, K. Takagi, and K. Adachi J. Med. Chem. 53 2010 3154
13. H. Tedesco-Silva, G. Mourad, B.D. Kahan, J.G. Boira, W. Weimar, S. Mulgaonkar, B. Nashan, S. Madsen, B. Charpentier, P. Pellet, and Y. Vanrenterghem Transplantation 77 2004 1826
14. K. Budde, R.L. Schmouder, R. Brunkhorst, B. Nashan, P.W. Lücker, T. Mayer, S. Choudhury, A. Skerjanec, G. Kraus, and H.H. Neumayer J. Am. Soc. Nephrol. 13 2002 1073
15. H. Kurata, K. Otsuki, K. Kusumi, M. Kurono, M. Terakado, T. Seko, H. Mizuno, T. Ono, H. Hagiya, M. Minami, S. Nakade, and H. Habashita Bioorg. Med. Chem. Lett. 21 2011 1390
16. 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
17. Y. Sanada, T. Mizushima, Y. Kai, J. Nishimura, H. Hagiya, H. Kurata, H. Mizuno, E. Uejima, and T. Ito Plos One 6 2011 e23933
18. M.P. Reddy, and G.S.K. Rao J. Org. Chem. 46 1981 5371
19. G. Verardo, P. Geatti, E. Pol, and A.G. Giumanini Can. J. Chem. 80 2002 779
20. D.A. Evans, J. Bartroli, and T.L. Shih J. Am. Chem. Soc. 103 1981 2127
21. D.A. Evans, A.S. Kim, R. Matternich, and V.J. Novack J. Am. Chem. Soc. 120 1998 5921