Rapid synthesis and properties of (±)-6-Deoxy-6-fluoro-myo-inositol-1,4,5-tris(phosphate) an analogue of myo-inositol-1,4,5-tris(phosphate)

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 10, 1996, Pages 1175-1178

  Guédat, Philippe ^a   Poitras, Marc ^b   Spiess, Bernard ^a   Guillemette, Gaetan ^b   Schlewer, Gilbert ^a  

^a Laboratoire de Pharmacochimie   (France)

^b UNIVERSITY OF SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

6 DEOXY 6 FLUOROINOSITOL 1,4,5 TRIPHOSPHATE; FLUORINE; HYDROXYL GROUP; INOSITOL DERIVATIVE; UNCLASSIFIED DRUG;

ADRENAL CORTEX; ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; ENDOPLASMIC RETICULUM; MICROSOME; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; RECEPTOR AFFINITY;

EID: 0029952293     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00193-X     Document Type: Article

References (23)

1. Berridge, M.J.; Irvine, R.F. Nature, 1984, 312, 315-321.
2. Berridge, M.J. Mol. Cell. Endocrinol. 1994, 98, 119-124.
3. Worley, P.F.; Baraban, J.M.; Supattapone, S.; Wilson, V.S.; Snyder, S.H. J. Biol. Chem. 1987, 262, 12132-12136.
4. Schmitt, L.; Bortmann, P.; Schlewer, G.; Spiess, B. J. Chem. Soc. ,Perkin Trans. 2, 1993, 2257-2263.
5. Schmitt, L.; Schlewer, G.; Spiess, B. Biochim. Biophys. Acta, 1991, 1075, 139-140.
6. Schmitt, L.; Spiess, B.; Schlewer, G. Bioorg. Med. Chem. Lett. 1995, 5, 1225-1230.
7. Kozikowski, A.P.; Ognyanov, V.I.; Fauq, A.H.; Nahorski, S.R.; Wilcox, R.A. J. Am. Chem. Soc. 1993, 115, 4429-4434.
8. Schmitt, L.; Spiess, B.; Schlewer, G. Tetrahedron Lett. 1992, 33, 2013-2016.
9. Bonis, D.; Sezan, A.; Mauduit, P.; Cleophax, J.; Gero, S.D.; Rossignol, B. Biochem. Biophys. Res. Commun. 1991, 175, 894-900.
10. Potter, B.V.L. Phosphorus Sulfur and Silicon, 1993, 73, 143-146.
11. Ley, S.V.; Parra, M.; Redgrave, J.L.; Sternfeld, F. Tetrahedron, 1990, 46, 4995-5026.
12. Massy, D.J.; Wyss, P. Helv. Chim. Acta, 1990, 73, 1037-1040.
13. Gigg, J.; Gigg, R.; Martin-Zamora, E. Tetrahedron Lett. 1993, 34, 2827-2830.
14. Offer, J.L.; Voorheis, H.P.; Metclafe, J.C.; Smith, G.A. J. Chem. Soc. ,Perkin Trans. 2, 1992, 953-960.
15. Jiang, C.; Schedler, D.J.A.; Morris, P.E., Zayed, A.H.A.; Baker, D.C. Carbohydr. Res. 1990, 207, 277-285.
16. 4).
17. Yang, S.S.; Chiang, Y.C.P.; Beattie, T.R. Carbohydr. Res. 1993, 249, 259-263.
18. Yang, S.S.; Beattie, T.R.; Shen, T.Y. Synthetic Comm. 1986, 16, 131-138.
19. Ballereau, S.; Guédat, P.; Spiess, B.; Rehnberg, N.; Schlewer, G. Tetrahedron Lett. 1995, 36, 7449-7450.
20. Perich, J.W.; Johns, R.B. Tetrahedron Lett. 1987, 28, 101-102.
21. Poitras, M.; Bernier, S., Richard, D.; Servant, M.; Guillemette, G. J. Biol. Chem. 1993, 268, 24078-24082.
22. Cozzone, P.J.; Jardetzky, O. Biochemistry, 1976, 15 (22), 4853-4859.
23. Mernissi Arifi, K.; Schmitt, L.; Schlewer, G.; Spiess, B. Anal. Chem. 1995, 67, 2567-2574.