Synthesis and growth inhibitory properties of glucosamine-derived glycerolipids

Organic Letters

Volumn 3, Issue 2, 2001, Pages 197-200

  Yang, Guangli ^a   Franck, Richard W ^a   Bittman, Robert ^b   Samadder, Pranati ^c   Arthur, Gilbert ^c  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b CITY UNIVERSITY OF NEW YORK   (United States)

^c UNIVERSITY OF MANITOBA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; GLUCOSAMINE; GLYCOLIPID;

ARTICLE; CELL CULTURE; CELL DIVISION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; FEMALE; HUMAN; MALE; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CELL DIVISION; FEMALE; GLUCOSAMINE; GLYCOLIPIDS; HUMANS; MALE; MOLECULAR STRUCTURE; TUMOR CELLS, CULTURED;

EID: 0035945770     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006783a     Document Type: Article

References (50)

1. Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, FL; 1995.
2. (b) Levy, D.; Tang, C. The Synthesis of C-Glycosides; Pergamon: Oxford, U.K.; 1995.
3. (c) Beau, J.-M.; Gallagher, T. Top. Curr. Chem. 1997, 187, 1-54.
4. Nicotra, F. Top. Curr. Chem. 1997, 187, 55-83.
5. (e) Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959.
6. 2. We use the word "exact" to characterize the analogue. It is not possible to review the many bioactive C-glycoside materials that do not have an exact O-analogue for comparison. To cite a few notable cases: (a) Schmidt, R. R.; Dietrich, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1328-1329.
7. (b) Michael, K.; Wittman, V.; Konig, W.; Sandow, J.; Kessler, H. Int. J. Peptide Protein Res. 1996, 48, 59-70.
8. (c) Nagy, J. O.; Wang, P.; Gilbert, J. H.; Schefer, M. E.; Hill, T. G.; Callstrom, M. R.; Bednarski, M. D. J. Med. Chem. 1992, 35, 4501-4502.
9. (d) Vyplel, H.; Scholz, D.; Macher, I.; Schindlmaier, K.; Schutze, E. J. Med. Chem. 1991, 34, 2759-2767. Refs 1a and 1b should be consulted for in-depth surveys of bioactive C-glycosides.
10. Espinosa, J.-F.; Canada, F. J.; Asensio, J. L.; Martin-Pastor, M.; Dietrich, H.; Martin-Lomas, M.; Schmidt, R. R.; Jiminez-Barbero, J. J. Am. Chem. Soc. 1996, 118, 10862-10871.
11. (b) Espinosa, J.-F.; Montero, E.; Vian, A.; Garcia, J. L.; Dietrich, H.; Schmidt, R. R.; Martin-Lomas, M.; Imberty, A.; Canada, F. J.; Jiminez-Barbero, J. J. Am. Chem. Soc. 1998, 120, 1309-1318.
12. Wei, A.; Haudrechy, A.; Audin, C.; Hyuk-Sang, J.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160-2169.
13. Ravishankar, R.; Surolia, A.; Vijayan, M.; Lim, S.; Kishi, Y. J. Am. Chem. Soc. 1998, 120, 11297-11303.
14. Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432-9436.
15. Wang, J.; Kovac, P.; Sinay, P., Glaudemans, C. P. J. Carbohydr. Res. 1998, 308, 191-193.
16. Tsuruta, O.; Yuasa, H.; Kurono, S.; Hashimoto, H. Bioorg. Med. Chem. Lett. 1999, 9, 807-810.
17. Acton, E. M.; Ryan, K. J.; Tracy, M.; Arora, S. K. Tetrahedron Lett. 1986, 27, 4245-4248.
18. (b) Welch, S. C.; Levine, J. A.; Arimilli, M. N. Synth. Commun. 1993, 23, 131-134.
19. Yang, G.; Franck, R. W.; Byun, H.-S.; Bittman, R.; Samadder, P.; Arthur, G. Org. Lett. 1999, 1, 2149-2151.
20. Erukulla, R. K.; Zhou, X.; Samadder, P.; Arthur, G.; Bittman, R. J. Med. Chem. 1996, 39, 1545-1548.
21. Paquette, L. A. Org. React. 1977, 25, 1-71.
22. (b) Guziec, F. S., Jr.; San Filippo, L. J. Tetrahedron 1988, 44, 6241-6285.
23. (c) Oae, S.; Uchida, Y. (Chapter 12); Braverman, S. (Chapter 13) In The Chemistry of Sulfones and Sufoxides; Patai, S., Ed.; Wiley: New York, 1988.
24. (d) Clough, J. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, Chapter 3.8.
25. Belica, P. A.; Franck, R. W. Tetrahedron Lett. 1998, 39, 8225-8228.
26. (b) Ref 10.
27. (c) Griffin, F. K.; Murphy, P. V.; Patterson, D. E.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 8179-8182.
28. (d) Alcaraz, M-L.; Griffin, F. K.; Patterson, D. E.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 8183-8186.
29. (e) Taylor, R. J. K.; Griffin, F. K.; Paterson, D. E. Angew. Chem., Int. Ed. 1999, 38, 2939-2942.
30. (f) Campbell, A. D.; Paterson, D. E.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Chem. Commun. 1999, 1599-1600.
31. (g) Falconer, R. A.; Toth, I. 20th International Carbohydrate Symposium, Hamburg, Aug. 28-Sept. 2, 2000, Poster B-348.
32. Roe, B. A.; Boojamra, C. G.; Griggs, J. L.; Bertozzi, C. R. J. Org. Chem. 1996, 61, 6442-6445. "Unfortunately, C-glycosyl derivatives of 2-amino sugars are among the most difficult to prepare as a result of the incompatibility of neighboring nitrogen-based functional groups (i.e., amides, carbamates, and azides) with common C-glycosylation strategies."
33. Free-radical methods: (a) ref 14.
34. (b) Gaurat, O.; Xie, J.; Valery, J.-M. Tetrahedron Lett. 2000, 41, 1187-1189.
35. (c) Junker, H.-D.; Phung, N.; Fessner, W.-D. Tetrahedron Lett. 1999, 40, 7063-7066.
36. (d) Cui, J.; Horton, D. Carbohydr. Res. 1998, 309, 319-330. Organosamarium methods:
37. (e) Andersen, L.; Munch, L.; Beau, J.-M.; Skrydstrup, T. Synlett 1998, 1393-1395.
38. (f) Urban, D.; Skrydstrup, T.; Beau, J.-M. J. Org. Chem. 1998, 63, 2507-2516. Organolithium methods:
39. (g) Burkhart, F.; Kessler, H. Tetrahedron Lett. 1998, 39, 255-256.
40. (h) Schafer, A.; Thiem, J. J. Org. Chem. 2000, 65, 24-29. Wittig methods:
41. (i) Xie, J.; Molina, A.; Czemecki, S. J. Carbohydr. Chem. 1999, 18, 481-498.
42. Horton, D.; Wolfrom, M. L. J. Org. Chem. 1962, 27, 1794-1799.
43. Park, W. K. C.; Meunier, S. J.; Zanini, D.; Roy, R. Carbohydr. Lett. 1995, 1, 179-184.
44. Kunesch, N.; Meit, C.; Poisson, J. Tetrahedron Lett. 1987, 28, 3569-3572.
45. This protection scheme was implemented (i) to replace KOH-sensitive acetates and (ii) to avoid alkylations with benzyl bromide, which would react with the amide function.
46. 3 is much higher than using the material that has been stored for 1 month in the desiccator.
47. Both Taylor's group and ours have observed clean β-C-glycoside formation upon hydrogenation deoxyglycals, almost certainly due to a chairlike transition state when the hydrogen is transferred to the α-face. Conversely, β-face approach of hydrogen requires a twist-boat like TS during H-transfer.
48. King, S. A.; Pipik, B.; Thompson, A. S.; Decamp, A.; Verhoeven, T. R. Tetrahedron Lett. 1995, 36, 4563-4566.
49. Samadder, P.; Byun, H.-S.; Bittman, R.; Arthur, G. Anticancer Res. 1998, 18, 465-470.
50. Hu, Y.; Meullet, E. J.; Qiao, L.; Berggren, M. M.; Powis, G.; Kozikowski, A. P. Tetrahedron Lett. 2000, 41, 7415-7418.