New cytotoxic furoquinones obtained from terpenyl-1,4-naphthoquinones and 1,4-anthracenediones

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 21, 2006, Pages 7231-7240

  Miguel del Corral, José M ^a   Castro, M Angeles ^a   Oliveira, Alaide B ^b   Gualberto, Simone A ^b   Cuevas, Carmen ^c   Feliciano, Arturo San ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

^c PHARMAMAR S A   (Spain)

Author keywords

1,4 Anthracenediones; Cytotoxicity; Furo 1,2 quinones; Furo 1,4 quinones; Terpenylnaphthoquinones

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 2 CHLORO 5,5(8,8) DIMETHYL 5,6,7,8 TETRAHYDROANTHRACENE 1,4 DIONE; 2 CHLORO 7(6) (4 METHYL 3 PENTENYL) 1,4 NAPHTHOQUINONE; 2,3 DICHLORO 5,5 DIMETHYL 5,6,7,8 TETRAHYDROANTHRACENE 1,4 DIONE; 5,5 DIMETHYL 5,6,7,8 TETRAHYDROANTHRACENE 1,4 DIONE; 6 (4 METHYL 3 PENTENYL) 1,4 NAPHTHOQUINONE; 6 (4 METHYLPENTYL) 1,4 NAPHTHOQUINONE; ANTHRAQUINONE DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; CYTOTOXICITY; DRUG EFFECT; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; OXIDATION; POLYMERIZATION; REACTION ANALYSIS;

ANTINEOPLASTIC AGENTS; CELL LINE; CELL LINE, TUMOR; CELL SURVIVAL; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; QUINONES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 33748789839     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.06.053     Document Type: Article

References (35)

1. O'Brien P.J. Chem. Biol. Interact. 80 (1991) 1-41
2. Monks T.J., Hanzlik R.P., Cohen G.M., Ross D., and Graham D.G. Toxicol. Appl. Pharmacol. 112 (1992) 2-16
3. Owton W.M. J. Chem. Soc., Perkin Trans. 1 (1999) 2409-2420
4. Thomson R.H. In: ApSimon J. (Ed). Total Synthesis of Natural Products Vol. 8 (1992), John Wiley, New York
5. Foye W.O. Cancer Chemotherapeutic Agents (1995), ACS, Washington, DC
6. Plyta Z.F., Li T., Papageorgiou V.P., Mellidis A.S., Assomopoulou A.N., Pitsinos E.N., and Couladouros E.A. Bioorg. Med. Chem. Lett. 8 (1998) 3385-3390
7. Miller M.G., Rodgers A., and Cohen G.M. Biochem. Pharmacol. 35 (1986) 1177-1184
8. Salmon-Chemin L., Buisine E., Yardley V., Kohler S., Debreu M.A., Landry V., Sergheraert C., Croft S.L., Krauth-Siegel R.L., and Davioud-Charvet E. J. Med. Chem. 44 (2001) 548-565
9. Madhusudana Rao M., and Kingston D.G.I. J. Nat. Prod. 45 (1982) 600-604
10. Hayashi T., Smith F.T., and Lee K.H. J. Med. Chem. 30 (1987) 2005-2008
11. Ribeiro-Rodrigues R., dos Santos W.G., Oliveira A.B., Snieckus V., Zani C.L., and Romanha A.J. Bioorg. Med. Chem. Lett. 5 (1995) 1509-1512
12. Thomson R.H. Naturally Occurring Quinones IV. Recent Advances (1997), Blackie A&P, London
13. Piggott M.J. Tetrahedron 61 (2005) 9929-9954
14. Zani C.L., Oliveira A.B., and Starling S.M. Quim. Nova 17 (1994) 43-52
15. Hooker S.C. J. Chem. Soc. 69 (1896) 1355
16. Sartori M.F. Chem. Rev. 63 (1963) 279
17. Miguel de Corral J.M., Gordaliza M., Castro M.A., Mahiques M.M., Chamorro P., Molinari A., García-Grávalos M.D., Broughton H.B., and San Feliciano A. J. Med. Chem. 44 (2001) 1257-1267
18. Miguel de Corral J.M., Gordaliza M., Castro M.A., Mahiques M.M., San Feliciano A., and García Grávalos M.D. Bioorg. Med. Chem. 6 (1998) 31-41
19. Miguel de Corral J.M., Castro M.A., Gordaliza M., Martín M.L., Oliveira A.B., Gualberto S.A., García-Grávalos M.D., and San Feliciano A. Arch. Pharm. Pharm. Med. Chem. 335 (2002) 427-437
20. Miguel del Corral J.M., Castro M.A., Gordaliza M., Martín M.L., Gualberto S.A., Gamito A.M., Cuevas C., and San Feliciano A. Bioorg. Med. Chem. 13 (2005) 631-644
21. Miguel del Corral J.M., Castro M.A., Gordaliza M., Martín M.L., Gamito A.M., Cuevas C., and San Feliciano A. Bioorg. Med. Chem. 14 (2006) 2816-2827
22. Castro M.A., Miguel de Corral J.M., Gordaliza M., Gamito A.M., Gualberto S.A., Batista R., and San Feliciano A. Synthesis (2005) 3202-3208
23. Roberge G., and Brassrd P. J. Org. Chem. 46 (1981) 4161-4166
24. Biosvert L., and Brassard P. J. Org. Chem. 53 (1988) 4052-4059
25. Grunwell J.R., Karipides A., Wigal C.T., Heinzman S.W., Parlow J., Surso J.A., Clayton L., Fleitz F.J., Daffner M., and Stevens J.E. J. Org. Chem. 56 (1991) 91-95
26. Tou J.S., and Reusch W. J. Org. Chem. 45 (1980) 5012-5014
27. Kobayashi, S., Jorgensen, K. A. Eds. Cycloaddition Reactions in Organic Chemistry; Wiley-VCH: Weinheim, 2001.
28. Ferreira V.F., Pinto A.V., Pinto M.C.F.R., daCruz M.C., and Clarino A. Synth. Commun. 19 (1989) 1061-1069
29. Dudley K.H., and Miller H.W. J. Org. Chem. (1967) 2341-2344
30. Kuo H.-S., Hotta K., Yogo M., and Yoshina S. Synthesis (1979) 188-189
31. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Waren J.T., Bokesch H., Kenney S., and Boyd M.R. J. Natl. Cancer Inst. 82 (1990) 1107-1112
32. Faircloth G.T., Stewart D., and Clement J.J. J. Tissue Cult. Meth. 11 (1988) 201-205
33. Kongkathip N., Kongkathip B., Siripong P., Sangma C., Luangkamin S., Niyomdecha M., Pattanapa S., Piyaviriyagul S., and Kongsaeree P. Bioorg. Med. Chem. 11 (2003) 3179-3191
34. Goulard M.O.F., Zani C.L., Tonholo J., Freitas L.R., Abreu F.C., Oliveira A.B., Raslan D.S., Starling S., and Chiari E. Bioorg. Med. Chem. Lett. 7 (1997) 2043-2048
35. Abreu F.C., Ferraz P.A.L., and Goulard M.O.F. J. Braz. Chem. Soc. 13 (2002) 19-35