The design, synthesis, and evaluation of novel conformationally rigid analogues of sialyl Lewis(x)

Bioorganic and Medicinal Chemistry

Volumn 6, Issue 12, 1998, Pages 2421-2439

  Murphy, Paul V ^a,c   Hubbard, Rod E ^a   Manallack, David T ^b   Wills, Ruth E ^b   Montana, John G ^b   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b Chiroscience Ltd   (United Kingdom)

^c UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Cell adhesion; Naphthalenes; Selectin inhibitors; Sialyl lewis(x); Tetralins

Indexed keywords

CARBOHYDRATE DERIVATIVE; ENDOTHELIAL LEUKOCYTE ADHESION MOLECULE 1; RECOMBINANT PROTEIN; TUMOR NECROSIS FACTOR ALPHA;

ARTICLE; CELL ADHESION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION;

EID: 0032408865     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(98)80017-5     Document Type: Article

References (45)

1. Lasky, L. A. Ann. Rev. Biochem. 1995, 64, 113.
2. Springer, T. A. Nature 1990, 346, 425.
3. (a) Lowe, J. B.; Stoolman, L. M.; Nair, R. P.; Larsen, R. D.; Berhend, T. L.; Marks, R. M. Cell 1990, 63, 475.
4. (b) Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A.; Hakomori, S.-I.; Paulson, J. C. Science 1990, 250, 1130.
5. (c) Wong, C. H.; Moris-Varas, F.; Hung, S.-C.; Marron, T. G.; Lin, C.-C.; Gong, K. W.; Weitz-Schmidt, G. J. Am. Chem. Soc. 1997, 119, 8152.
6. (a) Ichikawa, Y.; Halcomb, R. L.; Wong, C. H. Chem. Br. 1994, 117.
7. (b) Bertozzi, C. R. Chem. Biol. 1995, 2, 703.
8. Graves, B. J.; Crowther, R. L.; Chandran, C.; Rumberger, J. M.; Li, S.; Huang, K.-S.; Presky, D. H.; Familletti, P. C.; Walitzky, B. A.; Burns, D. K. Nature 1994, 367, 532.
9. Cooke, R. M.; Hale, R. S.; Lister, S. G.; Shah, G.; Weir, M. P. Biochemistry 1994, 33, 10591.
10. Kogan, T. P.; Revelle, B. M.; Tapp, S.; Scott, D.; Beck, P. J. J. Biol. Chem. 1995, 270, 14047.
11. Weis, W. I.; Kahn, R.; Fourme, R.; Drickamer, K.; Hendrickson, W. A. Science 1991, 360, 1608.
12. Roy, R.; Hasegawa, A.; Kiso, M. In Carbohydrates in Drug Design; Witczak, Z. J.; Nieforth, K. A., Eds.; Marcel Dekker: New York, 1997; pp 85-135 and 137-155.
13. (a) Wong, C. H.; Moris-Varas, F.; Hung, S.-C.; Marron, T. G.; Lin, C.-C.; Gong, K. W.; Weitz-Schmidt, G. J. Am. Chem. Soc. 1997, 119, 8152.
14. (b) Hanessian, S.; Reddy, G. V.; Huynh, H. K.; Pan, J.; Padatella, S. Bioorg. Med. Chem. Lett. 1997, 7, 2729.
15. (c) Kolb, H. C. Bioorg. Med. Chem. Lett. 1997, 7, 2485.
16. (d) Toepfer, A.; Kretzschmar Bioorg. Med. Chem. Lett. 1997, 7, 1311.
17. (e) Huang, B.-G.; Locke, R. D.; Jain, R. K.; Matta, K. L. Bioorg. Med. Chem. Lett. 1997, 7, 1157.
18. (f) Miyauchi, H.; Yuri, M.; Tanaka, M.; Kawamura, N.; Hayashi, M. Bioorg. Med. Chem. Lett. 1997, 7, 985.
19. (g) Bänteli, R.; Ernst, B. Tetrahedron Lett. 1997, 38, 4059.
20. (h) Narasinga Rao, B. N.; Anderson, M. B.; Musser, J. H.; Gilbert, J. H.; Schaefer M. E.; Foxall, C.; Bradley, B. K. J. Biol. Chem. 1994, 269, 19663.
21. (i) Prodger, J. C.; Bamford, M. J.; Gore, P. M.; Holmes, D. S.; Saez, V.; Ward, P. Tetrahedron Lett. 1995, 36, 2339.
22. (j) Kaila, N.; Yu, H. A.; Xiang, Y. Tetrahedron Lett. 1995, 36, 5503.
23. (k) Liu, A.; Dillon, K.; Campbell, R. M.; Cox, D. C.; Huryn, D. M. Tetrahedron Lett. 1996, 37, 3785.
24. (l) Kogan, T. P.; Dupre, B.; Keller, K. M.; Scott, I. L.; Bui, H.; Market, R. V.; Beck P. J.; Voytus, J. A.; Revelle, B. M.; Scott D. J. Med. Chem. 1995, 38, 4976.
25. (m) Wu, S. H.; Shimazaki, M.; Liu, C. C.; Qiao, L.; Moree, W. J.; Weitz-Schmidt, G.; Wong C.-H. Angew. Chem., Int., Ed., Engl. 1996, 35, 88.
26. (n) Uchiyama T.; Vassilev, V. P.; Kajimoto, T.; Wong, W.; Huang, H.; Liu, C. C.; Wong C.-H. J. Am. Chem. Soc. 1995, 117, 5395.
27. (o) Huang, H.; Wong, C.-H. J. Org. Chem. 1995, 60, 3100.
28. (p) Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzen, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826.
29. (q) Yarema, K. J.; Bertozzi, C. R. Curr. Opin. Chem. Biol. 1998, 2, 49.
30. (r) Kogan, T. P.; Dupre, B.; Bui, H.; McAbee, K. L.; Kassir, J. M.; Scott, I. L.; Hu, X.; Vanderslice, P.; Beck, P. J.; Dixon, R. A. F J. Med. Chem. 1998, 41, 1099.
31. (r) Tsukida, T.; Hiramatsu, Y.; Tsujishita; H.; Kiyoi, M.; Kurokawa, K.; Moriyama, H.; Ohmoto, H.; Wada, Y.; Saito, T.; Kondo, H. J. Med. Chem. 1997, 40, 3534.
32. (s) Yoshino, K.; Ohmoto, H.; Kondo, N.; Tsujishita; H.; Hiramatsu, Y.; Inoue, Y.; Kondo, H.; Ishida, H.; Kiso, M.; Hasegawa, A. J. Med. Chem. 1997, 40, 455.
33. (t) Kolb, H. C.; Ernst, B. Chem. Eur. J. 1997, 3, 1571.
34. Murphy, P. V.; Hubbard, R. E.; Manallack, D. T.; Montana, J. G.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3273.
35. Scheffler, K.; Ernst, E.; Katopodis, A.; Magnani; J. L.; Wang, W. T.; Weisemann, R.; Peters, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1841.
36. Gerlach, U.; Wollmann, T. Tetrahedron Lett. 1992, 33, 5499.
37. Lonn, H. Carbohydr. Res. 1985, 139, 105.
38. Lemieux, R. U.; Hendriks, K. B.; Stick, R. V.; James, K. J. Am. Chem. Soc. 1975, 97, 4056.
39. Cabre, J.; Palomo, A. L. Synthesis 1984, 413.
40. Chen, Q. Y.; Yang, Z.-Y. Tetrahedron Lett. 1986, 27, 1171.
41. 2) were investigated in an attempt to deprotect benzyl ethers in tetralins, but these reactions gave complex product mixtures. See Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd Edn; Wiley & Sons: New York, 1991; p 49.
42. (a) Vaporicyan, A. A.; Jones, M. L.; Ward, P. A. J. Immunol. Methods 1993, 159, 93.
43. (b) Boschelli, D. H.; Kramer, J. B.; Connor, D. T.; Lesch, M. E.; Schrier, D. J.; Ferin, M. A.; Wright, C. D. J. Med. Chem. 1994, 37, 717.
44. (c) Welply, J. K.; Abbas, S. Z.; Scudder, P.; Keene, J. L.; Broschat, K.; Casnocha, S.; Gorka, C.; Steininger, C.; Howard, S. C.; Schmuke, J. J.; Graneto, M.; Rotsaert, J. M.; Manger, I. D.; Jacob, G. S. Glycobiology 1994, 4, 259.
45. Schexnayder, M. A.; Engel, P. S. J. Am. Chem. Soc. 1975, 97, 4828.