Synthesis and inhibition of cancer cell proliferation of (1,3′)-bis-tetrahydroisoquinolines and piperazine systems

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 9, 2007, Pages 2598-2602

  Aubry, Sylvain ^a,b,c,d,e,f   Pellet Rostaing, Stéphane ^a,b,c,d,e,f   dit Chabert, Jérémie Fournier ^g   Ducki, Sylvie ^g   Lemaire, Marc ^a,b,c,d,e,f  

^a UNIVERSITÉ LYON 1   (France)

^b CNRS   (France)

^c UNIVERSITÉ DE LYON   (France)

^d UNIVERSITÉ LYON 1   (France)

^e UNIVERSITÉ DE LYON   (France)

^f CPE LYON   (France)

^g UNIVERSITY OF SALFORD   (United Kingdom)

Author keywords

Cancer cell proliferation; Flow cytometry; Piperazine systems; Synthesis

Indexed keywords

ALKALOID; PIPERAZINE DERIVATIVE; TETRAHYDROISOQUINOLINE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CELL CYCLE; CELL CYCLE G0 PHASE; CELL CYCLE G1 PHASE; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL CYCLE S PHASE; CELL PROLIFERATION; CELL STRAIN K 562; CELL STRAIN MCF 7; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; FLOW CYTOMETRY; HUMAN; HUMAN CELL; IC 50; LEUKEMIA L 1210; LEUKEMIA P 388; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; X RAY ANALYSIS;

EID: 33947727168     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.01.108     Document Type: Article

References (41)

1. Scott J., and Williams R.M. Chem. Rev. 102 (2002) 1669
2. Rinehart K.L., Holt T.G., Fregeau N.L., Perun Jr. T.J., Seigler D.S., Wilson G.R., and Shield L.S. Pure Appl. Chem. 62 (1990) 1277
3. Wright A.E., Forleo D.A., Gunawardana G.P., Gunasekera S.P., Koehn F.E., and McConnel O.J. J. Org. Chem. 55 (1990) 4508
4. Rinehart K.L., Holt T.G., Fregeau N.L., Keifer P.A., Sun F., Li H., and Martin D.G. J. Org. Chem. 55 (1990) 4512
5. Sakai R., Rinehart K.L., Guan Y., and Wang A.H.-J. Proc. Nat. Acad. Sci. U.S.A. 89 (1992) 11456
6. Sakai R., Jares-Erijaman E., Manzanares I., Elipe M.V., and Rinehart K.L. J. Am. Chem. Soc. 118 (1996) 9017
7. Aune G.J., Furuta T., and Pommier Y. Anti-Cancer Drugs 13 (2002) 545
8. Corey E.J., Gin D.Y., and Kania R.S. J. Am. Chem. Soc. 118 (1996) 9202
9. Martinez E.J., and Corey E.J. Org. Lett. 2 (2000) 993
10. Endo A., Yanagisawa A., Abe M., Tohma S., Kan T., and Fukuyama T. J. Am. Chem. Soc. 124 (2002) 6552
11. Chen J., Chen X., Bois-Choussy M., and Zhu J. J. Am. Chem. Soc. 128 (2006) 87
12. Zheng S., Chan C., Furuuchi T., Wright B.J.D., Zhou B., Guo J., and Danishefsky S.J. Angew. Chem., Int. Ed. 45 (2006) 1754
13. Martinez E.J., Owa T., Schreiber S.L., and Corey E.J. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 3496
14. Myers A.G., and Plowright A.T. J. Am. Chem. Soc. 124 (2002) 12969
15. Myers A.G., and Lanman B.A. J. Am. Chem. Soc. 123 (2001) 5114
16. Ong C.W., Chang Y.A., Wu J.-W., and Cheng C.-C. Tetrahedron 59 (2003) 8245
17. Lane J.W., Chen Y., and Williams R.M. J. Am. Chem. Soc. 127 (2005) 12684
18. Lane J.W., Estevez A., Mortara K., Callan O., Spencer J.R., and Williams R.M. Bioorg. Med. Chem. Lett. 16 (2006) 3180
19. Liu Z.-Z., Wang Y., Tang Y.-F., Chen S.-Z., Chen X.-G., and Li H.-Y. Bioorg. Med. Chem. Lett. 16 (2006) 1282
20. Ceballos P.A., Pérez M., Cuevas C., Francesch A., Manzanares I., and Echavarren A.M. Eur. J. Org. Chem. (2006) 1926
21. Puthongking P., Patarapanich C., Amnuoypol S., Suwanborirux K., Kubo A., and Saito N. Chem. Pharm. Bull. 54 (2006) 1010
22. Koizumi Y.-I., Inamura K.-I., Kubo A., and Saito N. Heterocycles 70 (2006) 477
23. Gomez-Monterey I.M., Campiglia P., Bertamino A., Mazzoni O., Diurno M.V., Novellino E., and Grieco P. Tetrahedron 62 (2006) 8083
24. González J.F., Avendaño C., and de la Cuesta E. Bioorg. Med. Chem. 15 (2007) 112
25. Pommier Y., Kolhagen G., Bailly C., Waring M., Mazumder A., and Kohn K.W. Biochemistry 35 (1996) 13303
26. Moore II B.M., Seaman F.C., Wheelhouse R.T., and Hurley L.H. J. Am. Chem. Soc. 120 (1998) 2490
27. Aubry S., Pellet-Rostaing S., Fenet R., and Lemaire M. Tetrahedron Lett. 47 (2006) 1319
28. Cox E.D., and Cook J.M. Chem. Rev. 95 (1995) 1797
29. Kametani T., Fukumoto K., Agui H., Yagi H., Kigasawa K., Sugushura H., Hiiragi M., Hayasaka T., and Ishimaru M. J. Chem. Soc. (C) (1968) 112
30. Kametani T., Kigasawa K., Hiiragi M., and Ishimaru H. J. Heterocycl. Chem. 7 (1970) 51
31. Jurczak J., and Golebiowski A. Chem. Rev. 89 (1989) 149
32. Crystallographic data (excluding structure factors) for 11 and 17 in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 287225 and 286961. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
33. Chan C., Heid R., Zheng S., Guo J., Zhou B., Furuuchi T., and Danishefsky S.J. J. Am. Chem. Soc. 127 (2005) 4596
34. Mosman T.J. Immunol. Methods 65 (1983) 55
35. Edmonson J.M., Armstrong L.S., and Martinez A.O. J. Tissue Culture Methods 11 (1988) 15
36. McGown A.T., Poppitt D.G., Swindel R.G., and Fox B.W. Br. J. Cancer 36 (1984) 1833
37. Rice J.A., Crothers D.M., Pinto A.L., and Lippard S.J. Proc. Natl. Acad. Sci. U.S.A. 85 (1988) 4158
38. Jin S., Gorfajn B., Faircloth G., and Scotto K.W. Proc. Natl. Acad. Sci. U.S.A. 97 (2001) 6775
39. Erba E., Bergamaschi D., Bassano L., Damia G., Ronzoni S., Faircloth G.T., and D'Incalci M. Eur. J. Cancer 37 (2001) 97
40. Takebayashi Y., Goldwaser F., Urasaki Y., Kohlhagen G., and Pommier Y. Clin. Cancer Res. 7 (2001) 185
41. Martinez E.J., Corey E.J., and Owa T. Chem. Biol. 8 (2001) 1151