Potential sialyltransferase inhibitors based on neuraminyl substitution by hetaryl rings

Carbohydrate Research

Volumn 342, Issue 3-4, 2007, Pages 558-566

  Mathew, Bini ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Heterocycles; Inhibitors; Phosphonates; Sialyltransferases; Transition state analogs

Indexed keywords

HETEROCYCLES; PHOSPHONATES; SIALYLTRANSFERASES; TRANSITION STATE ANALOGS;

BENZENE; ESTERS; PHOSPHORUS COMPOUNDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ENZYME INHIBITION;

BENZOTHIAZOLE; BENZOTHIOPHENE; BENZOXAZOLE DERIVATIVE; ENZYME INHIBITOR; METHYLPHOSPHONIC ACID; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SIALYLTRANSFERASE; SIALYLTRANSFERASE INHIBITOR; THIAZOLE; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INACTIVATION; PRIORITY JOURNAL; SUBSTITUTION REACTION;

CYTIDINE MONOPHOSPHATE N-ACETYLNEURAMINIC ACID; ENZYME INHIBITORS; PHOSPHONIC ACIDS; SIALYLTRANSFERASES;

EID: 33846508612     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2006.08.016     Document Type: Article

References (33)

1. Morgenthaler J., Kemner J., and Brossmer R. Biochem. Biophys. Res. Commun. 171 (1990) 860-866
2. Rosenberg A. Biology of Sialic Acids (1995), Plenum, New York
3. Reutter W., Stäsche R., Stehling P., and Baum O. In: Gabius H.J., and Gabius S. (Eds). Glycosciences (1997), Chapman and Hall, Weinheim 245-259
4. Schauer R. Glycoconjugate J. 17 (2000) 485-499
5. Dall'Olio F., and Chiricolo M. Glycoconjugate J. 18 (2001) 841-850
6. Jogeeswaran G. Adv. Cancer Res. 38 (1983) 289-350
7. Collard J.G., Schijen J.F., Bikker A., LaRiviere G., Bolscher J.G.M., and Roos E. Cancer Res. 46 (1986) 3521-3527
8. Petrick A.T., Meterissian S., Steele G., and Thomas P. Clin. Exp. Metastasis 12 (1994) 108-116
9. Hennet T., Chui D., Paulson J.C., and Marth J.D. Proc. Natl. Acad. Sci. 95 (1998) 4504-4509
10. Harvey B.E., Toth C.A., Wagner H.E., Steele G.D., and Thomas P. Cancer Res. 52 (1992) 1775-1779
11. Schaub C., Müller B., and Schmidt R.R. Glycoconjugate J. 15 (1998) 345-354
12. Müller B., Martin T.J., Schaub C., and Schmidt R.R. Tetrahedron Lett. 39 (1988) 509-512
13. Brunner M., and Horenstein B.A. Biochemistry 39 (2000) 2261-2268
14. Horenstein B.A., and Brunner M. Biochemistry 37 (1998) 289-297
15. Horenstein B.A., and Brunner M. J. Am. Chem. Soc. 118 (1996) 10371-10379
16. Müller B., Schaub C., and Schmidt R.R. Angew. Chem. 110 (1998) 3021-3024
17. Angew. Chem., Int. Ed. 37 (1998) 2893-2897
18. Amann F., Schaub C., Müller B., and Schmidt R.R. Chem. Eur. J. 4 (1998) 1106-1115
19. Schaub C., Müller B., and Schmidt R.R. Eur. J. Org. Chem. (2000) 1745-1758
20. Dufner G., Schwörer R., Müller B., and Schmidt R.R. Eur. J. Org. Chem. (2000) 1467-1482
21. Schwörer R., and Schmidt R.R. J. Am. Chem. Soc. 124 (2002) 1632-1637
22. Skropeta D., and Schmidt R.R. Tetrahedron: Asymmetry 14 (2003) 265-273
23. Skropeta D., Schwörer R., and Schmidt R.R. Bioorg. Med. Chem. Lett. 13 (2003) 3351-3354
24. Skropeta D., Schwörer R., Haag T., and Schmidt R.R. Glycoconjugate J. 21 (2004) 205-219 221-225
25. Jung K.-H., and Schmidt R.R. In: Wong C.H. (Ed). Carbohydrate-Based Drug Discovery (2003), Wiley-VCH 609-659
26. Jung K.-H., Schwörer R., and Schmidt R.R. Trends Glycosci. Glycotechnol. 15 (2003) 275-289
27. Gibbs D.E., and Larsen C. Synthesis (1984) 410-412
28. Felber R., and Lohse P.A. Tetrahedron Lett. 39 (1998) 2067-2070
29. Beaucage S.L., and Caruthers M.H. Tetrahedron Lett. 22 (1981) 1859-1862
30. Schmidt R.R., and Frische K. Bioorg. Med. Chem. Lett. 3 (1993) 1747-1750
31. Kajihara Y., Ebata T., Koseki K., Kodama H., Matsushita H., and Hashimoto H. J. Org. Chem. 60 (1995) 5732-5735
32. Rohloff J.C., Alfredson T.V., and Schwartz M.A. Tetrahedron Lett. 35 (1994) 1011-1014
33. Vetelino M.G., and Coe J.W. Tetrahedron Lett. 35 (1994) 219-222