Design and synthesis of conformationally constrained 3-(N-alkylamino) propylphosphonic acids as potent agonists of sphingosine-1-phosphate (S1P) receptors

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 19, 2004, Pages 4861-4866

  Yan, Lin ^a   Hale, Jeffrey J ^a   Lynch, Christopher L ^a   Budhu, Richard ^a   Gentry, Amy ^a   Mills, Sander G ^a   Hajdu, Richard ^a   Keohane, Carol Ann ^a   Rosenbach, Mark J ^a   Milligan, James A ^a   Shei, Gan Ju ^a   Chrebet, Gary ^a   Bergstrom, James ^a   Card, Deborah ^a   Rosen, Hugh ^a   Mandala, Suzanne M ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; LEAD; PROLINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SPHINGOSINE 1 PHOSPHATE; SPHINGOSINE 1 PHOSPHATE RECEPTOR AGONIST; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG EFFICACY; DRUG POTENCY; DRUG SYNTHESIS; LYMPHOCYTE COUNT; MOUSE; NONHUMAN;

ANIMALS; CHO CELLS; CRICETINAE; DRUG DESIGN; HUMANS; MOLECULAR CONFORMATION; PHOSPHONIC ACIDS; RECEPTORS, LYSOSPHINGOLIPID; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 4444287013     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.07.049     Document Type: Article

References (26)

1. K. Budde, R.L. Schmouder, R. Brunkhorst, B. Nashan, P.W. Lucker, T. Mayer, S. Choudhury, A. Skerjanec, G. Kraus, and H.H. Neumayer J. Am. Soc. Nephrol. 13 2002 1073 1083
2. K. Budde, R.L. Schmouder, B. Nashan, R. Brunkhorst, P.W. Lucker, T. Mayer, L. Brookman, J. Nedelman, A. Skerjanec, T. Bohler, and H.-H. Neumayer Am. J. Transplant. 3 2003 846 854
3. B.D. Kahan, J.L. Karlix, R.M. Ferguson, A.B. Leichtman, S. Mulgaonkar, T.A. Gonwa, A. Skerjanec, R.L. Schmouder, and L. Chodoff Transplantation 7 2003 1079 1084
4. Ebeling, T.; Fishman, M. Novartis' 2003 'R&D Day', 19 November 2003
5. S. Mandala, R. Hajdu, J. Bergstrom, E. Quackenbush, J. Xie, J. Milligan, R. Thornton, G.J. Shei, D. Card, C. Keohane, M. Rosenbach, J. Hale, C.L. Lynch, K. Rupprecht, W. Parsons, and H. Rosen Science 296 2002 346 349
6. 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 21457
7. A. Billich, F. Bornancin, P. Dévay, D. Mechtcheriakova, N. Urtz, and T. Baumruker J. Biol. Chem. 278 2003 47408 47415
8. M. Matloubian, C.G. Lo, G. Cinamon, M.J. Lesneski, Y. Xu, V. Brinkmann, M. Allende, R.L. Proia, and J.G. Cyster Nature 427 2004 355 360
9. M.L. Allende, J.L. Dreier, S. Mandala, and R.L. Proia J. Biol. Chem. 279 2004 15396 15401
10. J.J. Hale, G. Doherty, L. Toth, Z. Li, S.G. Mills, R. Hajdu, C.A. Keohane, M. Rosenbach, J. Milligan, G.-J. Shei, G. Chrebet, J. Bergstrom, D. Card, H. Rosen, and S. Mandala Bioorg. Med. Chem. Lett. 14 2004 3495 3499
11. J.J. Hale, W. Neway, S.G. Mills, R. Hajdu, C.A. Keohane, M. Rosenbach, J. Milligan, G.-J. Shei, G. Chrebet, J. Bergstrom, D. Card, G.C. Koo, S.L. Koprak, J.J. Jackson, H. Rosen, and S. Mandala Bioorg. Med. Chem. Lett. 14 2004 3351 3355
12. P. Beak, A. Basu, D.J. Gallagher, Y.S. Park, and S. Thayumanavan Acc. Chem. Res. 29 1996 552 560
13. S.V. Ley, J. Norman, W.P. Griffith, and S.P. Marsden Synthesis 1994 639 666
14. Y. Terao, H. Kotaki, N. Imai, and K. Achiwa Chem. Pharm. Bull. 33 1985 896 898
15. J. Kehler, B. Ebert, O. Dahl, and P. Krogsgaard-Larsen J. Chem. Soc., Perkin Trans. 1998 3241 3243
16. 1 receptor (Ref. 6). Although such effect has not been studied in 3-(N-alkylamino)propylphosphonic acid series, it is conceivably unlikely that an alpha-hydroxyl group will exert a substantial adverse effect on the binding
17. T.J. Wilkinson, N.W. Stehle, and P. Beak Org. Lett. 2 2000 155 158
18. P. Beak, and W.K. Lee J. Org. Chem. 58 1993 1109 1117
19. 50 value within a deviation of 10%
20. D.L. Comins, and J.D. Brown Tetrahedron Lett. 27 1986 4549 4552
21. Z. Li, S. Racha, L. Dan, H. El-Subbagh, and E. Abushanab J. Org. Chem. 58 1993 5779 5783
22. I. Mori, Y. Kimura, T. Nakano, S-i Matsunaga, G. Iwasaki, A. Ogawa, and K. Hayakawa Tetrahedron Lett. 38 1997 3543 3546
23. T. Nagasaka, A. Tsukada, and F. Hamaguchi Heterocycles 24 1986 2015 2022
24. D.H.R. Barton, and S.W. McCombie J. Chem. Soc., Perkin Trans. 1 1975 1574 1585
25. M. Forrest, S.-Y. Sun, R. Hajdu, J. Bergstrom, D. Card, G. Doherty, J. Hale, C.A. 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. Pharm. Exp. Therap. 309 2004 758 768
26. 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 13848