Structure-activity relationship of short-chain sphingoid bases as inhibitors of sphingosine kinase

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 21, 1999, Pages 3175-3180

  De Jonghe, Steven ^a   Van Overmeire, Ilse ^a   Poulton, Samantha ^b   Hendrix, Chris ^c   Busson, Roger ^c   Van Calenbergh, Serge ^a   De Keukeleire, Denis ^a   Spiegel, Sarah ^b   Herdewijn, Piet ^a,c  

^a GHENT UNIVERSITY   (Belgium)

^b GEORGETOWN UNIVERSITY MEDICAL CENTER   (United States)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG ANALOG; ENZYME INHIBITOR; PHOSPHOTRANSFERASE; SPHINGANINE; SPHINGOSINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME INHIBITOR INTERACTION; FLUORINATION; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE;

CELL LINE; ENZYME INHIBITORS; FLUORINE COMPOUNDS; HUMANS; LYSOPHOSPHOLIPIDS; MOLECULAR STRUCTURE; PHOSPHOTRANSFERASES (ALCOHOL GROUP ACCEPTOR); SPHINGOSINE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

SPHINGIODEA;

EID: 0033230427     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00554-5     Document Type: Article

References (19)

1. Olivera, A. & Spiegel, S. Nature 1993, 365, 557-559.
2. Edsall, L.C.; Pirianov, G.G. & Spiegel, S. J. Neurosci. 1997, 17, 6952-6960.
3. Cuvillier, O.; Pirianov, G.; Kleuser, B.; Vanek, P.G.; Coso, O.A.; Gutkind, J.S. & Spiegel, S. Nature 1996, 381, 800-803.
4. Van Brocklyn, J.R.; Lee, M.J.; Menzeleev, R.; Olivera, A.; Edsall, L.; Cuvillier, O.; Thomas, D.M.; Coopman, P.J.P.; Thangada, S.; Hla, T. & Spiegel, S. J. Cell. Biol. 1998, 142, 229-240.
5. Sadahira, Y.; Ruan, F.; Hakomori, S. & Igarashi, Y. Proc. Natl. Acad. Sci. USA 1992, 89, 9686-9690.
6. Yatomi, Y.; Ruan, F.; Hakomori, S. & Igarashi, Y. Blood 1995, 86, 193-202.
7. Van Brocklyn, J.R.; Tu, Z.; Edsall, L.C.; Schmidt, R.R. & Spiegel, S. J. Biol. Chem. 1999, 274, 4626-4632.
8. Buehrer, B.M. & Bell, R.M. J. Biol. Chem. 1992, 267, 3154-3159.
9. Edsall, L.C.; Van Brocklyn, J.R.; Cuvillier, O.; Kleuser, B. & Spiegel, S. Biochemistry 1998, 37, 12892-12898.
10. Van Overmeire, I.; Boldin, S.A.; Dumont, F.; Van Calenbergh, S.; Slegers, G.; De Keukeleire, D.; Futerman, A.H. & Herdewijn, P. J. Med. Chem. 1999, 42, 2697-2705.
11. De Jonghe, S.; Van Overmeire, I.; Gunst, J.; De Bruyn, A.; Hendrix, C.; Van Calenbergh, S.; Busson, R.; De Keukeleire, D.; Philippé, J. & Herdewijn, P. Bioorg. Med. Chem. Lett.1999, 9, 3159-3164.
12. Herold, P. Helv. Chim. Acta 1988, 71, 354-362.
13. Garner, P. & Park, J.M. J. Org. Chem. 1987, 52, 2361-2364.
14. 2), 3.0 (1 H, m, H-C(2)), 3.65 (2 H, dd, J = 6.9 Hz and 11.7 Hz, 2 H-(C(1)), 3.75 (1 H, dd, J = 4.1 Hz and 11.7 Hz, H-C(3)).
15. b-C(1) and H-C(3)), 7.13 (1 H, m, arom H), 7.20-7.25 (4 H, m, arom H).
16. Futagawa, S.T.I. & Shiba, T. Bull. Chem. Soc. Jpn. 1973, 46, 3308-3310; Rich, D.H. & Sun, E.T.O. J. Med. Chem. 1980, 23, 27-33.
17. Futagawa, S.T.I. & Shiba, T. Bull. Chem. Soc. Jpn. 1973, 46, 3308-3310; Rich, D.H. & Sun, E.T.O. J. Med. Chem. 1980, 23, 27-33.
18. The synthesis of L-threo-3-fluoro-sphingosine and its allylic rearranged isomer has been described using 2-chloro-1,1,2-trifluorotriethylamine as fluorinating agent (Kozikowski, A.P. & Wu, J.P. Tetrahedron Lett. 1990, 31, 4309-4312). However, on using DAST, a higher yield of the desired 3-fluorinated compound was obtained (26% vs. 13%).
19. Kohama, T.; Olivera, A.; Edsall, L.; Nagiec, M.M.; Dickson, R. & Spiegel, S. J. Biol. Chem. 1998, 273, 23722-23728.