3-Arylamino and 3-alkoxy-nor-β-lapachone derivatives: Synthesis and cytotoxicity against cancer cell lines

Journal of Medicinal Chemistry

Volumn 53, Issue 1, 2010, Pages 504-508

  Da Silva Jr , Eufrânio N ^a   De Deus, Clara F ^a   Cavalcanti, Bruno C ^b   Pessoa, Cláudia ^b   Costa Lotufo, Letícia V ^b   Montenegro, Raquel C ^b   De Moraes, Manoel O ^b   Pinto, Maria Do Carmo F R ^c   De Simone, Carlos A ^d,e   Ferreira, Vitor F ^f   Goulart, Marilia O F ^d   Andrade, Carlos Kleber Z ^a   Pinto, Antônio V ^c  

^a UNIVERSITY OF BRASILIA   (Brazil)

^b FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

^c FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^d FEDERAL UNIVERSITY OF ALAGOAS   (Brazil)

^e UNIVERSITY OF SÃO PAULO   (Brazil)

^f FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; BETA LAPACHONE; DOXORUBICIN;

ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL;

CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NAPHTHOQUINONES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 74849110255     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900865m     Document Type: Article

References (22)

1. (a) Hillard, E. A.; de Abreu, F. C.; Ferreira, D. C. M.; Jaouen, G.; Goulart, M. O. F.; Amatore, C. Electrochemical parameters and techniques in drug development, with an emphasis on quinones and related compounds. Chem. Commun. 2008, 2612-2628.
2. (b) da Silva, A. J. M.; Netto, C. D.; Pacienza-Lima, W.; Torres-Santos, E. C.; Rossi-Bergmann, B.; Maurel, S.; Alexis Valentin, A.; Costa, P. R. R. Antitumoral, antileishmanial and antimalarial activity of pentacyclic 1,4-naphthoquinone derivatives. J. Braz. Chem. Soc. 2009, 20, 176-182.
3. (a) Plyta, Z. F.; Li, T.; Papageorgiou, V. P.; Mellidis, A. S.; Assimopoulou, A. N.; Pitsinos, E. N.; Couladouros, E. A. Inhibition of topoisomerase I by naphthoquinone derivatives. Bioorg. Med. Chem. Lett. 1998, 8, 3385-3390.
4. (b) Oliveira, C. G. T.; Frederico, F. M.; Ferreira, V, F.; Freitas, C. C.; Rabello, R. F.; Carballido, J. M.; Corra, L. C. D. Synthesis and antimicrobial evaluation of 3-hydrazino-naphthoquinones as analogs of lapachol. J. Braz. Chem. Soc. 2001, 12, 339-345.
5. Kitagawa, R. R.; da Fonseca, L. M.; Ximenes, V. F.; Khalil, N. M.; Vilegas, W.; Raddi, M. S. G. Ascorbic acid potentiates the cytotoxicity of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin. Phytochemistry 2008, 69, 2205-2208.
6. Phillips, R. M.; Jaffar, M.; Maitland, D. J.; Loadman, P. M.; Shnyder, S. D.; Steans, G.; Copper, P. A.; Race, A.; Patterson, A. V.; Stratford, I. J. Pharmacological and biological evaluation of a series of substituted 1,4-naphthoquinone bioreductive drugs. Biochem. Pharmacol. 2004, 68, 2107-2116.
7. (a) Adams, N.; Blake, C.; Broadhurst, M. J.; Bushnell, D. J.; Hassall, C. H.; Hartmann, H. R.; Keech, E.; Stratton, A. R.; Thomas, G. J. Synthesis and antitumor activity of 9-[(carbamoyloxy) alkyl]anthracyclines a novel class of anthracycline derivatives. J. Med. Chem. 1990, 33, 2380-2384.
8. (b) Chung, Y.; Im, J. K.; Lee, S.; Cho, H. Synthesis and cytotoxicity of anilinomethyl-1,4-naphthoquinones. Bull. Korean Chem. Soc. 2004, 25, 1408-1410.
9. (c) Yamashita, Y.; Saitoh, Y.; Ando, K.; Takahashi, K.; Ohno, H.; Nakano, H. Saintopin, a new antitumor antibiotic with topoisomerase II dependent DNA cleavage activity, from Paecilomyces. J. Antibiot. 1990, 43, 1344-1346.
10. Ferreira, D. C. M.; Goulart, M. O. F.; Moreira, M. S. A.; Pinto, A. V.; Tapsoba, I.; Arbault, S.; Amatore, C. Ex vivo activities of β-lapachone and R-lapachone on macrophages: a quantitative pharmacological analysis based on amperometric monitoring of oxidative bursts by single cells. ChemBioChem 2009, 10, 528-538.
11. da Silva Júnior, E. N.; de Souza, M. C. B. V.; Fernandes, M. C.; Menna-Barreto, R. F. S.; Pinto, M. C. F. R.; Lopes, F. A.; de Simone, C. A.; Andrade, C. K. Z.; Pinto, A. V.; Ferreira, V. F.; de Castro, S. L. Synthesis and anti-Trypanosoma cruzi activity of derivatives from nor-lapachones and lapachones. Bioorg. Med. Chem. 2008, 16, 5030-5038.
12. da Silva Júnior, E. N.; de Souza, M. C. B. V.; Pinto, A. V.; Pinto, M. C. F. R.; Goulart, M. O. F.; Pessoa, C.; Costa-Lotufo, L.; Montenegro, R. C.; Moraes, M. O.; Ferreira, V. F. Synthesis and potent antitumor activity of new arylamino derivatives of nor-β-lapachone and nor-α-lapachone. Bioorg. Med. Chem. 2007, 15, 7035-7041.
13. da Silva Júnior, E. N.; de Moura, M. A. B. F.; Pinto, A. V.; Pinto, M. C. F. R.; de Souza, M. C. B. V.; Araújo, A. J.; Pessoa, C.; Costa-Lotufo, L. V.; Montenegro, R. C.; de Moraes, M. O.; Ferreira, V. F.; Goulart, M. O. F. Cytotoxic, trypanocidal activities and physicochemical parameters of nor-β-lapachone-based 1,2,3-triazoles. J. Braz. Chem. Soc. 2009, 20, 635-643.
14. Pinto, A. V.; Pinto, M. C. F. R.; de Oliveira, C. G. T. Synthesis of the α- and nor-β-lapachones. Properties in acid and reactions with N-bromosuccinimide. An. Acad. Bras. Cienc. 1982, 54, 107-114.
15. da Silva Júnior, E. N.; Simone, C. A.; Goulart, M. O. F.; Andrade, C. K. Z.; Sales, S. R.; Pinto, A. V. 3-(2,4-Dibromoanilino)-2,2-dimethyl-2,3- dihydronaphtho[1,2-b]furan-4,5-dione: a new substituted arylamino nor-β-lapachone derivative. Acta Crystallogr. E 2008, 64, o2348.
16. Fieser, L. F.; Fieser, M. Naphthoquinone antimalarials. XII. The Hooker oxidation reaction. J. Am. Chem. Soc. 1948, 70, 3215-3222.
17. (a) Silva, T. M. S.; Camara, C. A.; Barbosa, T. P.; Soares, A. Z.; da Cunha, L. C.; Pinto, A. C.; Vargas, M. D. Molluscicidal activity of synthetic lapachol amino and hydrogenated derivatives. Bioorg. Med. Chem. 2005, 13, 193-196.
18. (b) Camara, C. A.; Pinto, A. C.; Rosa, M. A.; Vargas, M. D. Secondary amines and unexpected 1-aza-anthraquinones from 2-methoxylapachol. Tetrahedron 2001, 57, 9569-9574.
19. 13C chemical shifts of new arylamino derivatives of ortho-naphthofuranquinones. Magn. Reson. Chem. 2008, 46, 1158-1162.
20. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.
21. Pérez-Sacau, E.; Díaz-Pe~nate, R. G.; Estévez-Braun, A.; Ravelo, A. G.; Garcia-Castellano, J. M.; Pardo, L.; Campillo, M. Synthesis and pharmacophore modeling of naphthoquinone derivatives with cytotoxic activity in human promyelocytic leukemia HL-60 cell line. J. Med. Chem. 2007, 50, 696-706.
22. Jimenez, P. C.; Fortier, S. C.; Lotufo, T. M. C.; Pessoa, C.; Moraes, M. E. A.; Moraes, M. O.; Costa-Lotufo, L. V. Biological activity in extracts of ascidians (Tunicata, Ascidiacea) from the northeastern Brazilian coast. J. Exp. Mar. Biol. Ecol. 2003, 287, 93-101.