Synthesis and biological evaluation of novel benzoxazinic analogues of ellipticine

Tetrahedron Letters

Volumn 51, Issue 30, 2010, Pages 3987-3990

  Mousset, Deborah ^a   Rabot, Rémi ^a   Bouyssou, Pascal ^a   Coudert, Gérard ^a   Gillaizeau, Isabelle ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOXAZINE DERIVATIVE; ELLIPTICINE; HETEROCYCLIC COMPOUND; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ANNULATION REACTION; ANTINEOPLASTIC ACTIVITY; ARTICLE; COLON ADENOCARCINOMA; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN TISSUE; LEUKEMIA CELL; TUMOR CELL LINE;

EID: 77953687186     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.123     Document Type: Article

References (47)

1. Goodwin S., Smith A.F., and Horning E.C. J. Am. Chem. Soc. 81 (1959) 1903
2. Knölker H. J. Chem. Lett. 38 (2009) 8
3. Wang J.C. Annu. Rev. Biochem. 65 (1996) 635
4. Monks N.R., Blankey D.C., East S.J., Dowell R.I., Caluete J.A., Curtin N.J., Arris C.E., and Newell D.R. Eur. J. Cancer 11 (2002) 1543
5. LePez J.B., DzXuong N., Gosse C., and Paolett C. Proc. Natl. Acad. Sci. U.S.A. 71 (1974) 5078
6. Stiborová M., Sejhal J., Borěk-Dohalská L., Aimová D., Poliaková J., Forsterová K., Rupertová M., Wiessler J., Hudecěk J., Wiessler M., and Frei E. Cancer Res. 64 (2004) 8374
7. Poliaková J., Eckschlager T., Hraběta J., Hrěbačková J., Smutnỳ S., Frei E., Martínek R., and Stiborová M. Biochem. Pharmacol. 77 (2009) 1466
8. Stiborová M., Breuer A., Aimová D., Stiborová -Rupertová M., Wiessler M., and Frei E. Int. J. Cancer 107 (2003) 885
9. Gaddam V., and Nagarajan R. Tetrahedron Lett. 50 (2009) 1243
10. Caruso A., Voisin-Chiret A.S., Lancelot J.C., Sinicropi M.S., Garofalo A., and Rault S. Heterocycles 71 (2007) 2203
11. Auclair C. Arch. Biochem. Biophys. 259 (1987) 1
12. Gribble G.W. In: Brossi A. (Ed). The Alkaloids (1990), Academic Press, San Diego, CA 239
13. Knölker H.-J., and Reddy K.R. Chem. Rev. 102 (2002) 4303
14. Marsais F., Pineau P., Nivolliers F., Mallat M., Turck A., Godard A., and Queguiner G. J. Org. Chem. 57 (1992) 565
15. Gribble G.W. Synlett 28 (1991) 289
16. Gribble G.W., Saulnier M.G., Sibi M.P., and Obaza-Nutaitis J.A. J. Org. Chem. 49 (1984) 4518
17. Sainsbury M. Synthesis (1977) 437
18. Alvarez M., and Joule J.A. In: Saxton J.E. (Ed). The Chemistry of Heterocyclic Compounds (1994), Wiley, Chichester 261
19. Kansal V.K., and Potier P. Tetrahedron 42 (1986) 2389
20. Hewlins M.J.E., Oliveira-Campos A.-M., and Shannon P.V.R. Synthesis (1984) 289
21. Ishikura M., Hino A., Yaginuma T., Agata I., and Katagiri N. Tetrahedron 56 (2000) 193
22. Mal D., Senapati B.K., and Pahari P. Synlett (2005) 994
23. Miki Y., Hachiken H., and Yanase N. Org. Biomol. Chem. (2001) 2213
24. Caruso A., Lancelot J.-C., El-Kashef H., Sinicropi M.S., Legay R., Lesnard A., and Rault S. Tetrahedron 65 (2009) 10400
25. Gaddam V., and Nagaraja R. Tetrahedron Lett. 50 (2009) 1243
26. Ferlin M.G., Marzano C., Gandin V., Dall'Acqua S., and Dalla Via L. ChemMedChem 4 (2009) 363
27. Tsuchimoto T., Matsubayashi H., Kaneko M., Shirakawa E., and Kawakami Y. Angew. Chem., Int. Ed. 44 (2005) 1336
28. Martinez - Esperón M.F., Rodríguez D., Castedo L., and Saá C. Org. Lett. 7 (2005) 2213
29. Ruiz N., Bouyssou P., Marizis J.C., Madelmont J.C., and Coudert G. Heterocycl. Commun. 3 (1997) 509
30. Ayerbe N., Routier S., Gillaizeau I., Tardy S., and Coudert G. Lett. Org. Chem. 7 (2010) 121
31. Lepifre F., Buon C., Roger P.-Y., Bouyssou P., and Coudert G. Tetrahedron Lett. 45 (2004) 8257
32. Buon C., Chacun-Lefèvre L., Rabot R., Bouyssou P., and Coudert G. Tetrahedron 56 (2000) 605
33. Routier S., Peixoto P., Mérour J.Y., Coudert G., Dias N., Bailly C., Leonce S., and Caignard D.H. J. Med. Chem. 48 (2005) 1401
34. Lefoix M., Coudert G., Routier S., Pfeiffer B., Caignard D.H., Hickman J., Pierré A., Golsteyn R.M., Léonce S., Bossard C., and Mérour J.Y. Bioorg. Med. Chem. 16 (2008) 5303
35. Coudert, G.; Ayerbe, N.; Lepifre, F.; Routier, S.; Caignard, D. H.; Renard, P.; Hickman, J.; Pierré, A.; Léonce, S. WO 2004037831; Chem. Abstr. 2004, 140, 339333.
36. Kimura K., Usui Y., Hattori T., Yamakawa N., Goto H., Usui M., Okada S., Shirato K., and Tomoda A. Oncol. Rep. 19 (2008) 3
37. Ishihara M., Kawase M., Westman G., Samuelsson K., Motohashi N., and Sakagami H. Anticancer Res. 27 (2007) 4053
38. Khatib S., Bouzoubaa M., and Coudert G. Tetrahedron Lett. 39 (1998) 989
39. Beak P., and Snieckus V. Acc. Chem. Res. 15 (1982) 306
40. de Koning C.B., Rousseau A.L., and van Otterlo W.A.L. Tetrahedron 59 (2003) 7
41. Schlecker W., Huth A., Ottow E., and Mulzer J. J. Org. Chem. 60 (1995) 8414
42. Sibi M.P., Dankwardt J.W., and Snieckus V. J. Org. Chem. 51 (1986) 271
43. Gribble G.W., Saulnier M.G., Obaza-Nutaitis J.A., and Ketcha D.M. J. Org. Chem. 57 (1992) 5891
44. Wang Y., Li X., and Ding K. Tetrahedron: Asymmetry 13 (2002) 1291
45. Echavarren A.M., and Stille J.K. J. Am. Chem. Soc. 109 (1987) 5478
46. Coudert, G.; Lepifre, F.; Caignard, D. H.; Renard, P.; Hickman, J.; Pierré, A.; Kraus-Berthier, L. WO 2004037830; Chem. Abstr. 2004, 140, 339334.
47. Romero M., Renard P., Caignard D.-H., Atassi G., Solans X., Constans P., Bailly C., and Pujol M.D. J. Med. Chem. 50 (2007) 294