Synthesis of C-linked immobilized analogs of aloisine A by 'click' chemistry

Tetrahedron Letters

Volumn 50, Issue 7, 2009, Pages 741-744

  Haddoub, Rose ^a   Gueyrard, David ^a   Goekjian, Peter G ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Affinity chromatography; Immobilization; Protein kinase inhibitor; Structure activity relationship studies; 3+2 Cycloaddition

Indexed keywords

ALOISINE A; CYCLIN DEPENDENT KINASE INHIBITOR; UNCLASSIFIED DRUG;

AFFINITY CHROMATOGRAPHY; ARTICLE; CYCLOADDITION; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

EID: 58149094458     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.051     Document Type: Article

References (29)

1. Dhavan R., and Tsai L.H. Nat. Rev. Mol. Cell Biol. 2 (2001) 749-759
2. Morgan D. Annu. Rev. Cell Dev. Biol. 13 (1997) 261-291
3. See for example:. Cohen P. Nat. Rev. Drug Discovery 1 (2002) 309-315
4. Malumbres M., and Barbacid M. Nat. Rev. Cancer 1 (2001) 222-231
5. Fischer P.M. Curr. Opin. Drug Discovery Dev. 4 (2001) 623-634
6. Bain J., Plater L., Elliott M., Shapiro N., Hastie J., McLauchlan H., Klevernic I., Arthur J.S.C., Alessi D., and Cohen P. Biochem. J. 408 (2007) 297-315
7. See for example:. Trapp J., Jochum A., Meier R., Saunders L., Marshall B., Kunick C., Verdin E., Goekjian P., Sippl W., and Jung M. J. Med. Chem. 49 (2006) 7307-7316
8. Knockaert M., Greengard P., and Meijer L. TRENDS Pharmacol. Sci. 23 (2002) 417-425
9. Knockaert M., Gray N., Damiens E., Chang Y.-T., Grellier P., et al. Chem. Biol. 7 (2000) 411-422
10. Knockaert M., Gray N., Damiens E., Chang Y.T., Grellier P., Grant K., Fergusson D., Mottram J., Soete M., Dubremetz J.F., LeRoch K., Doerig C., Schultz P.G., and Meijer L. Chem. Biol. 7 (2000) 411-422
11. Knockaert M., Wieking K., Schmitt S., Leost M., Mottram J., Kunick C., and Meijer L. J. Biol. Chem. 277 (2002) 25493-25501
12. Meijer L., Skaltsounis A.L., Magiatis P., Polychronopoulos P., Knockaert M., Leost M., Ryan X.P., Vonica C.A., Brivanlou A., Dajani R., Crovace C., Tarricone C., Musacchio A., Roe S.M., Pearl L., and Greengard P. Chem. Biol. 10 (2003) 1255-1266
13. Bach S., Knockaert M., Reinhardt J., Lozach O., Schmitt S., and Baratte B. J. Biol. Chem. 280 (2005) 31208-31219
14. Mettey Y., Gompel M., Thomas V., Garnier M., Leost M., Ceballos-Picot I., et al. J. Med. Chem. 46 (2003) 222-236
15. Mapelli M., Massimiliano L., Crovace C., Seeliger M., Tsai L.H., Meijer L., and Musacchio A. J. Med. Chem. 48 (2005) 671-679
16. Corbel, C.; Haddoub, R.; Guiffant, D.; Lozach, O.; Gueyrard, D.; Lemoine, J.; Ratin, M.; Meijer, L.; Bach, S.; Goekjian, P.G., unpublished results.
17. Kolb H.C., Finn M.G., and Sharpless K.B. Angew. Chem., Int. Ed. 40 (2001) 2004-2021
18. Kolb H.C., and Sharpless K.B. Drug Discovery Today 8 (2003) 1128-1137
19. Vierfond J.M., Mettey Y., Mascrier-Demagny L., and Miocque M. Tetrahedron Lett. 22 (1981) 1219-1222
20. Eduardo F.M., Correa J., Irene R.M., and Ricardo R. Macromolecules 39 (2006) 2113-2120
21. 2Si: 300.1420; found: 300.1420.
22. Davis M., Wakefield B., and Wardell J. Tetrahedron 48 (1992) 939-952
23. 2Si: 448.2420; found: 448.2423.
24. 7S: 705.3070; found: 705.3068.
25. Lober S., and Gmeiner P. Tetrahedron 60 (2004) 8699-8702
26. Punna S., Kaltgrad E., and Finn M.G. Bioconjugate Chem. 16 (2005) 1536-1541
27. Tornøe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057-3064
28. Menzel K., Fischer E., DiMichele L., Frantz D., Nelson T., and Kress M. J. Org. Chem. 71 (2006) 2188-2191
29. 2, and 0.2 M EDTA to provide 26 as a white, UV-fluorescent gel, indicating the presence of immobilized 2. Further IR measurements indicated the disappearance of the azido group and the affinity chromatography results provided in the supplementary material demonstrate the presence of the immobilized aloisines.