New 1-C-(5-thio-D-xylopyranosyl) derivatives as potential orally active venous antithrombotics

Carbohydrate Research

Volumn 338, Issue 12, 2003, Pages 1271-1282

  Mignon, Laurent ^a   Goichot, Christophe ^a   Ratel, Philippe ^a   Cagnin, Gérald ^b   Baudry, Michel ^b   Praly, Jean Pierre ^b   Boubia, Benaïssa ^a   Barberousse, Véronique ^a  

^a Laboratoires Fournier SA   (France)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

1 C (5 Thio D xylopyranosyl) derivatives; Glycosidic linkage; Venous antithrombotics

Indexed keywords

BLOOD VESSELS; DERIVATIVES; DISEASES; FREE RADICALS; SYNTHESIS (CHEMICAL);

ANTITHROMBOTICS;

CARBOHYDRATES;

2 [(5 THIO BETA DEXTRO XYLOPYRANOSYL) 1 HYDROXYETHYL]BENZONITRILE; 4 CYANO 2' (5 THIO BETA DEXTRO XYLOPYRANOSYL)ACETOPHENONE; BLOOD CLOTTING FACTOR 10A; CARBOHYDRATE DERIVATIVE; FIBRINOLYTIC AGENT; THIOGLYCOSIDE; UNCLASSIFIED DRUG; XYLOSE; [2 (5 THIO BETA DEXTRO XYLOPYRANOSYL)ETHYL]BENZONITRILE;

ANIMAL; ANIMAL MODEL; ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONTROLLED STUDY; DISEASE MODEL; DRUG METABOLISM; DRUG SYNTHESIS; EXPERIMENTAL MODEL; MICROSOME; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION; SYNTHESIS; THROMBOSIS; VEIN THROMBOSIS;

EID: 0038697625     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(03)00147-2     Document Type: Article

References (50)

1. Bellamy F., Horton D., Millet J., Picart F., Samreth S., Chazan J.B. J. Med. Chem. 36:1993;898-903.
2. Samreth S., Barberousse V., Bellamy F., Horton D., Masson P., Millet J., Renaut P., Sepulchre C., Theveniaux J. Trends Recept. Res. 20:1993;41-59.
3. Bellamy F., Barberousse V., Martin N., Masson P., Millet J., Samreth S., Sepulchre C., Theveniaux J., Horton D. Euro. J. Med. Chem. 30:1995;101s-115s.
4. Samreth S., Barberousse V., Bellamy F., Horton D., Masson P., Millet J., Renaut P., Sepulchre C., Theveniaux J. Actual. Chim. Ther. 21:1994;23-33.
5. Okayama M., Kimata K., Suzuki S. J. Biochem. (Tokyo). 74:1973;1069-1073.
6. Schwartz N.B. J. Biol. Chem. 252:1977;6316-6321.
7. Guichard, J.P.; Guillou, F. Unpublished results.
8. Postema M.H.D. Tetrahedron. 48:1992;8545-8599.
9. Levy D.E., Tang C. The Chemistry of C-glycosides. 1995;Pergamon Elsevier Science Ltd, Oxford.
10. Postema M.H.D. C-Glycoside Synthesis. 1995;CRC Press, Boca Raton, FL.
11. Belosludtsev Y.Y., Bhatt R.K., Falck J.R. Tetrahedron Lett. 36:1995;5881-5882.
12. Wang X., Gross P.H. J. Org. Chem. 60:1995;1201-1206.
13. Mazeas D., Skrydstrup T., Beau J.M. Angew. Chem., Int. Ed. Engl. 34:1995;909-912.
14. Mata F.Z., Martinez M.B., Perez J.A.G. Carbohydr. Res. 225:1992;159-161.
15. Toshima K., Matsuo G., Tatsuta K. Tetrahedron Lett. 33:1992;2175-2178.
16. Jaramillo C., Knapp S. Synthesis. 1994;1-20.
17. Dheilly L., Frechou C., Beaupere D., Uzan R., Demailly G. Carbohydr. Res. 224:1992;301-306.
18. Lopez R., Fernandez-Mayoralas A. J. Org. Chem. 59:1994;737-745.
19. Boyd V.A., Drake B.E., Sulikowski G.A. J. Org. Chem. 58:1993;3191-3193.
20. Whistler R.L., Van Es T. J. Org. Chem. 28:1963;2303-2304.
21. Yuasa H., Tamura J.I., Hashimoto H. J. Chem. Soc., Perkin Trans. 1. 1990;2763-2769.
22. McAllister G.D., Taylor R.J.K. Tetrahedron Lett. 2001;1197-1200.
23. Gallagher M.J., Harvey S., Raston C.L., Sue R.E. J. Chem. Soc., Chem. Commun. 1988;289-290.
24. BeMiller J.N., Yadav M.P., Kalabokis V.N., Myers R.W. Carbohydr. Res. 200:1990;111-126.
25. Coxon B., Fletcher H.G. Jr. J. Am. Chem. Soc. 86:1964;922-925.
26. Allevi P., Anastasia M., Ciuffreda P., Frecchi A., Scala A. J. Chem. Soc., Perkin Trans. 1. 1989;1275-1280.
27. Kobayashi M., Shimadate T. Chem. Pharm. Bull. 34:1986;4069-4074.
28. Cai M.S., Qiu D.X. Carbohydr. Res. 191:1989;125-126.
29. Allevi P., Anastasia M., Ciuffreda P., Scala A. J. Carbohydr. Chem. 12:1993;209-222.
30. Garcia Lopez M.T., De las Heras F.G., San Felix A. J. Carbohydr. Chem. 6:1987;273-279.
31. Drew K.N., Gross P.H. J. Org. Chem. 56:1991;509-513.
32. Giese B., Dupuis J., Leising M., Nix M., Lindner H.J. Carbohydr. Res. 171:1987;329-341.
33. Tucker C.E., Magid T.N., Knochel P. J. Am. Chem. Soc. 114:1992;3983-3985.
34. Bihovsky R., Selick C., Giusti J. J. Org. Chem. 53:1988;4026-4031.
35. Panigot M.J., Curley R.W. Jr. J. Carbohydr. Chem. 13:1994;293-302.
36. Panigot M.J., Humphries K.A., Curley R.W. Jr. J. Carbohydr. Chem. 13:1994;303-321.
37. Ogawa T., Pernet A.G., Hanessian S. Tetrahedron Lett. 37:1973;3543-3546.
38. Hoffmann M.G., Schmidt R.R. Liebigs Ann. Chem. 1985;2403-2419.
39. Davidson A.H., Hughes L.R., Qureshi S.S., Wright B. Tetrahedron Lett. 29:1988;693-696.
40. Green M. J. Chem. Soc. 1963;1324-1327.
41. Mbongo A., Frechou C., Beaupère D., Uzan R., Demailly G. Carbohydr. Res. 246:1993;361-370.
42. Dawe R.D., Fraser-Reid B. J. Org. Chem. 49:1984;522-528.
43. Horton D., Koh D. Carbohydr. Res. 250:1993;231-247.
44. Theveniaux, J.; Millet, J. Unpublished results.
45. Condon S., Dupre D., Fargayrac G., Nedelec J.-Y. Eur. J. Org. Chem. 1:2002;105-111.
46. Bajic M., Kumar A., Boykin D.W. Heterocyclic Commun. 2:1996;135-140.
47. Yokokawa F., Asano T., Shioiri T. Tetrahedron. 57:2001;6311-6327.
48. Aggarwal V.K., Sheldon C.G., MacDonald G.J., Martin W.P. J. Am. Chem. Soc. 124:2002;10300-10301.
49. Samreth, S.; Millet, J.; Bellamy, F.; Bajgrowicz, J.; Barberousse, V. EP-365 397; Chem. Abstr. 1991, 114, 858.
50. Samreth, S.; Millet, J.; Bellamy, F.; Bajgrowicz, J.; Barberousse, V. EP-365 397; Chem. Abstr. 1991, 114, 858.