Studies on quinones. Part 44: Novel angucyclinone N-heterocyclic analogues endowed with antitumoral activity

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 24, 2008, Pages 10172-10181

  Valderrama, Jaime A ^a   Colonelli, Pamela ^a   Vásquez, David ^a   González, M Florencia ^a   Rodríguez, Jaime A ^b   Theoduloz, Cristina ^b  

^a PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

^b UNIVERSIDAD DE TALCA   (Chile)

Author keywords

Angucyclinones; Bioisoteric replacement; Cytotoxicity; N heterocyclic quinones

Indexed keywords

10 METHYL 3,4,7A,8,11,11A HEXAHYDRO 2H 5,8 DIAZABENZO[A]ANTHRACENE 1,7,12 TRIONE; 8 HYDROXY 3,4 DIHYDRO 2H BENZO[J]PHENANTHRIDINE 1,7,12 TRIONE; 8 HYDROXY 6 METHYL 3,4 DIHYDRO 2H BENZO[J]PHENANTHRIDINE 1,7,12 TRIONE; ANGUCYCLINE DERIVATIVE; ETOPOSIDE; HETEROCYCLIC COMPOUND; PYRIDAZINE DERIVATIVE; PYRIDINE DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; CYCLOADDITION; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; FIBROBLAST; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; ONE POT SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANTHRAQUINONES; ANTINEOPLASTIC AGENTS; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; TUMOR CELLS, CULTURED;

EID: 56349121749     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.10.064     Document Type: Article

References (40)

1. Valderrama J.A., Leiva H., Rodríguez J.A., Theoduloz C., and Schmeda-Hirshmann G. Bioorg. Med. Chem. 16 (2008) 3687
2. Rohr J., and Thiericke R. Nat. Prod. Rep. (1992) 103
3. Krohn K., and Rohr J. Top. Curr. Chem. 188 (1997) 127
4. Liu W.-C., Parker W.L., Slusarchyk D.S., Greenwood G.L., Graham S.F., and Meyers E. J. Antibiot. 23 (1970) 437
5. Hayakawa Y., Ha S.-C., Kim Y.L., Furihata K., and Seto H. J. Antibiot. 44 (1991) 1179
6. Kunstmann M.P., and Mitscher L.A. J. Org. Chem. 31 (1996) 2920
7. Oka M., Kamei H., Hamagishi Y., Omita K., Miyaki T., Konish M., and Oki T. J. Antibiot. 43 (1990) 967
8. Korynevska A., Heffeter P., Matselyukh B., Elbling L., Micksche M., Stoika R., and Berger W. Biochem. Pharmacol. 74 (2007) 1713
9. Carreño M.C., Urbano A., and Vitta C.D. Chem. Commun. (1999) 817
10. Carreño M.C., Urbano A., and Vitta C.D. Chem. Eur. J. 6 (2000) 906
11. Larsen D.S., O'Shea M.D., and Brooker S. Chem. Commun. (1996) 203
12. Boyd V.A., and Sulikowski G.A. J. Am. Chem. Soc. 117 (1995) 8472
13. Yamaguchi M., Okuma T., Horiguchi C., Ikeura C., and Minami T. J. Org. Chem. 57 (1992) 1647
14. Krohn K., Böker N., Flöke U., and Freund C. J. Org. Chem. 62 (1997) 2350
15. Kalogerakis A., and Groth U. Org. Lett. 5 (2003) 843
16. Burger A. Prog. Drug Res. 37 (1991) 287
17. Olesen P.H. Curr. Opin. Drug Discov. Dev. 4 (2001) 471
18. Krapcho A.P., Maresch M.J., Hacker M.P., Hazelhurst L., Menta E., Spinelli S., Beggiolin G., Giuliani F.C., Pezzoni P., and Tognella S. Curr. Med. Chem. 2 (1995) 803
19. Collet S., Remi J.-F., Cariou C., Lai{dotless}b S., Guingant A., Vu N.-Q., and Dujardin G. Tetrahedron Lett. 45 (2004) 4911
20. Vu N.-Q., Dujardin G., Collet S.C., Raiber E.-A., Guingant A.Y., and Michel Evain M. Tetrahedron Lett. 46 (2005) 7669
21. Benites J., Valderrama J.A., Rivera F., Rojo L., Campos N., Pedro P., and Nascimento M.S.J. Bioorg. Med. Chem. 16 (2008) 862
22. Valderrama J.A., González M.F., David Pessoa-Mahana D., Ricardo A., Tapia R.A., Houda Fillion H., Felix Pautet F., Rodríguez J.A., Theoduloz C., and Schmeda-Hirschmann G. Bioorg. Med. Chem. 14 (2006) 5003
23. Valderrama J.A., Espinoza O., González M.F., Tapia R.A., Rodríguez J.A., Theoduloz C., and Schmeda-Hirschmann G. Tetrahedron 62 (2006) 2631
24. Valderrama J.A., Zamorano C., González M.F., Prina E., and Fournet A. Bioorg. Med. Chem. 13 (2005) 4153
25. Valderrama J.A., Benites J., Cortés M., Pessoa-Mahana D., Prina E., and Fournet A. Bioorg. Med. Chem. 11 (2003) 4713
26. Tapia R.A., Alegría L., Pessoa C.D., Salas C., Cortés M., Valderrama J.A., Sarciron M.-E., Pautet F., Walchshofer N., and Fillon H. Bioorg. Med. Chem. 11 (2003) 2175
27. Valderrama J.A., Astudillo C., Tapia R.A., Prina E., Estrabaud E., Mahieux R., and Fournet A. Chem. Pharm. Bull. 50 (2002) 1215
28. Valderrama J.A., Benites J., Cortés M., Pessoa-Mahana D., Prina E., and Fournet A. Tetrahedron 58 (2002) 881
29. Valderrama J.A., Pessoa-Mahana D., Tapia R., Rojas de Arias A., Nakayama H., Torres S., Miret J., and Ferreira M.E. Tetrahedron 57 (2001) 8653
30. Preliminary communications on the synthetic access to these series has appeared:. Valderrama J.A., González M.F., Colonelli P., and Vásquez D. Synlett (2006) 2777
31. Valderrama J.A., and Vásquez D. Tetrahedon Lett. 49 (2008) 703
32. Rozeboom M.D., Tegmo-Larsson I.-M., and Houk K.N. J. Org. Chem. 46 (1981) 2338
33. Sanmartín C., Echeverría M., Mendívil B., Cordeu L., Cubedo E., García-Foncillas J., Font M., and Palopa J.A. Bioorg. Med. Chem. 13 (2005) 2031
34. Klutchko S.R., Hamby J.M., Boschelli D.H., Wu Z., Kraker A.J., Amar A.M., Hartl B.G., Shen C., Klohs W.D., Steinkampf R.W., Driscoll D.L., Nelson J.M., Elliott W.L., Roberts B.J., Stoner C.L., Vincent P.W., Dykes D.J., Panek R.L., Lu G.H., Major T.C., Dahring T.K., Hallak H., Bradford L.A., Showalter H.D.H., and Doherty A.M. J. Med. Chem. 41 (1998) 3276
35. Dorsey J.F., Jove R., Kraker A.J., and Wu J. Cancer Res. 60 (2000) 3127
36. Valderrama J.A., González M.F., and Valderrama C. Tetrahedron 55 (1999) 6039
37. Valderrama J.A., Araya-Maturana R., González F., Tapia R., Fariña F., and Paredes M.C. J. Chem. Soc. Perkin Trans. 1 (1991) 555
38. Rodríguez J.A., and Haun M. Planta Med. 65 (1999) 522
39. Kraus G.A., and Kirihara M. J. Org. Chem. 57 (1992) 3256
40. Schiel C., Oelgemöller M., Jürgen Ortner J., and Mattay J. Green Chem. 3 (2001) 224