Synthesis of cytotoxic aza analogues of jaspine B

Journal of Organic Chemistry

Volumn 75, Issue 22, 2010, Pages 7920-7923

  Rives, Arnaud ^a   Ladeira, Sonia ^b   Levade, Thierry ^b   Andrieu Abadie, Nathalie ^b   Génisson, Yves ^a  

^a UPS)   (France)

^b UNIVERSITÉ PAUL SABATIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AZA ANALOGUES; CYTOTOXIC; PYRROLIDINES; SPHINGOLIPIDS; TUMOR CELLS;

CYTOTOXICITY; STEREOCHEMISTRY;

CYCLIZATION;

4 AMINO 2 TETRADECYLPYRROLIDIN 3 OL; AMINOPYRROLIDINE; ENZYME INHIBITOR; JASPINE B; PYRROLIDINE DERIVATIVE; SPHINGOLIPID; SPHINGOSINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL VIABILITY; CYTOTOXICITY; HUMAN; HUMAN CELL; NONHUMAN; STAUDINGER REACTION; STEREOISOMERISM; SYNTHESIS; TUMOR CELL;

ANIMALS; CELL LINE, TUMOR; HUMANS; MELANOMA, EXPERIMENTAL; MICE; PYRROLIDINES; SPHINGOSINE; STEREOISOMERISM;

EID: 78449244314     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1014239     Document Type: Article

References (33)

1. Hirabayashi, Y.; Igarashi, Y.; Merrill, A. H. J. Sphingolipid Biology; Springer-Verlag: Tokyo, 2006.
2. Hannun, Y. A.; Obeid, L. M. Nat. Rev. Mol. Cell Biol. 2008, 9, 139-150
3. Ogretmen, B.; Hannun, Y. A. Nat. Rev. Cancer 2004, 4, 604-616
4. Ségui, B.; Andrieu-Abadie, N.; Jaffrézou, J.-P.; Benoist, H.; Levade, T. Biochim. Biophys. Acta 2006, 1758, 2104-2120
5. Lin, C. F.; Chen, C. L.; Lin, Y. S. Curr. Med. Chem. 2006, 13, 1609-1616
6. Modrak, D. E.; Gold, D. V.; Goldenberg, D. M. Mol. Cancer Ther. 2006, 5, 200-208
7. Morales, A.; Fernandez-Checa, J. C. Mini-Rev. Med. Chem. 2007, 7, 371-382
8. Salma, Y.; Lafont, E.; Therville, N.; Carpentier, S.; Bonnafe, M. J.; Levade, T.; Génisson, Y.; Andrieu-Abadie, N. Biochem. Pharmacol. 2009, 78, 477-485
9. Salma, Y.; Ballereau, S.; Ladeira, S.; Andrieu-Abadie, N.; Génisson, Y. Org. Biomol. Chem. 2010, 8, 3227-3243
10. Faugeroux, V.; Génisson, Y.; Andrieu-Abadie, N.; Colie, S.; Levade, T.; Baltas, M. Org. Biomol. Chem. 2006, 4, 4437-4439
11. Rives, A.; Génisson, Y.; Faugeroux, V.; Zedde, C.; Lepetit, C.; Chauvin, R.; Saffon, N.; Andrieu-Abadie, N.; Colie, S.; Levade, T.; Baltas, M. Eur. J. Org. Chem. 2009, 2474-2489
12. For a review of sphingolipids metabolism modulators: Delgado, A.; Casas, J.; Llebaria, A.; Abad, J. L.; Fabrias, G. ChemMedchem 2007, 2, 580-606
13. Boto, A.; Hernandez, D.; Hernandez, R. Tetrahedron Lett. 2009, 50, 3974-3977
14. For the use of such epoxyaldehydes in the synthesis of iminosugars see: Ayad, T.; Genisson, Y.; Baltas, M.; Gorrichon, L. Chem. Commun. 2003, 582-583
15. Ayad, T.; Génisson, Y.; Baltas, M. Org. Biomol. Chem. 2005, 3, 2626-2631
16. For the use of a related vinylation in the synthesis of iminosugars see: Ayad, T.; Génisson, Y.; Baltas, M.; Gorrichon, L. Synlett 2001, 866-868
17. Ayad, T.; Faugeroux, V.; Génisson, Y.; Andre, C.; Baltas, M.; Gorrichon, L. J. Org. Chem. 2004, 69, 8775-8779
18. For an in-depth study of this oxirane opening reaction see ref 5b.
19. Appel, R. Angew. Chem., Int. Ed. 1975, 14, 801-811
20. Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400
21. Razavi, H.; Polt, R. J. Org. Chem. 2000, 65, 5693-5706
22. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181-1183
23. Schwardt, O.; Veith, U.; Gaspard, C.; Jager, V. Synthesis-Stuttgart 1999, 1473-1490
24. 3 J correlation between the benzylic methylene protons and the C-1 (sphingolipid numbering), thus indicating an N-C-1 connection.
25. For a review on the Saudinger reaction see: Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1406
26. Legters, J.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1989, 30, 4881-4884
27. Thijs, L.; Porskamp, J. J. M.; Vanloon, A. A. W. M.; Derks, M. P. W.; Feenstra, R. W.; Legters, J.; Zwanenburg, B. Tetrahedron 1990, 46, 2611-2622
28. Legters, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 1-15 For a related process see: Chun, J.; He, L. L.; Byun, H. S.; Bittman, R. J. Org. Chem. 2000, 65, 7634-7640
29. 3.
30. For recent studies see: Rountree, J. S. S.; Butters, T. D.; Wormald, M. R.; Dwek, R. A.; Asano, N.; Ikeda, K.; Evinson, E. L.; Nash, R. J.; Fleet, G. W. J. Tetrahedron Lett. 2007, 48, 4287-4291
31. Choubdar, N.; Bhat, R. G.; Stubbs, K. A.; Yuzwa, S.; Pinto, B. M. Carbohydr. Res. 2008, 343, 1766-1777
32. Curtis, K. L.; Evinson, E. L.; Handa, S.; Singh, K. Org. Biomol. Chem. 2007, 5, 3544-3553
33. Rountree, J. S. S.; Butters, T. D.; Wormald, M. R.; Boomkamp, S. D.; Dwek, R. A.; Asano, N.; Ikeda, K.; Evinson, E. L.; Nash, R. J.; Fleet, G. W. J. ChemMedChem 2009, 4, 378-392