Synthesis and anticancer activity evaluation of new 2-alkylcarbonyl and 2-benzoyl-3-trifluoromethyl-quinoxaline 1,4-di-N-oxide derivatives

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 13, 2004, Pages 3711-3721

  Zarranz, Belén ^a   Jaso, Andrés ^a   Aldana, Ignacio ^a   Monge, Antonio ^a  

^a UNIVERSITY OF NAVARRA   (Spain)

Author keywords

Anticancer activity; Carbonyl quinoxalines 1,4 di N oxide; Synthesis

Indexed keywords

2 (2,2 DIMETHYLPROPANOYL) 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 2 ACETYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 2 ACETYL 6,7 DICHLORO 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 2 ACETYL 6,7 DIFLUORO 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 2 ACETYL 6,7 DIMETHYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 2 ACETYL 7 CHLORO 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 2 ACETYL 7 METHYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 2 ISOBUTYRYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 2 PROPIONYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 6,7 DICHLORO 2 (2,2 DIMETHYLPROPANOYL) 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 6,7 DICHLORO 2 ISOBUTYRYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 6,7 DICHLORO 2 PROPIONYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 6,7 DIFLUORO 2 ISOBUTYRYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 6,7 DIFLUORO 2 PROPIONYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 6,7 DIMETHYL 2 (2,2 DIMETHYLPROPANOYL) 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 6,7 DIMETHYL 2 ISOBUTYRYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 6,7 DIMETHYL 2 PROPIONYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 7 CHLORO 2 (2,2 DIMETHYLPROPANOYL) 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 7 CHLORO 2 ISOBUTYRYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 7 CHLORO 2 PROPIONYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 7 METHOXY 2 (2,2 DIMETHYLPROPANOYL) 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 7 METHOXY 2 ISOBUTYRYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 7 METHOXY 2 PROPIONYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 7 METHYL 2 (2,2 DIMETHYLPROPANOYL) 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 7 METHYL 2 ISOBUTYRYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; 7 METHYL 2 PROPIONYL 3 TRIFLUOROMETHYLQUINOXALINE 1,4 DI N OXIDE; ANTINEOPLASTIC AGENT; CARBONYL DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL GROWTH; CELL LINE; CELL TYPE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKEMIA CELL;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; QUINOXALINES;

EID: 2942606547     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.04.013     Document Type: Article

References (23)

1. Cheeseman G.W.H., Cookson R.F. Weissberger A., Taylor E.C. The Chemistry of Heterocyclic Compounds. Vol. 35:1979;1-27 J. Wiley and Sons, New York. 35-38
2. Porter A.E.A. Katrizky A.R., Rees C.W. Comprehensive Heterocyclic Chemistry. Vol. 3:1984;157-197 Pergamon, New York
3. Musatova I.S., Elina A.S., Padeiskaya E.N., Shipilova L.D., Yakobson G.G., Furin G.G. Khim. Farm. Zh. 16:1982;934
4. Musatova I.S., Elina A.S., Padeiskaya E.N. Khim. Farm. Zh. 16:1982;1063
5. Monge A., Gil M.J., Pascual M.A., Gastelurrutia M.A. An. R. Acad. Farm. 49:1983;37 Chem. Abstr. 99:1983;194924s
6. Monge A., Gil M.J., Pascual M.A., Gastelurrutia M.A. An. R. Acad. Farm. 49:1983;37 Chem. Abstr. 99:1983;194924s
7. Monge A., Gil M.J., Pascual M.A. An. R. Acad. Farm. 49:1983;199
8. Johnston, J. D. U.S. Patent 3,344,022, 1967
9. Galt, R. H. B. U.S. Patent 3,479,354, 1969
10. Schmid, W. Switz. Patent C.H. 630,908, 1982
11. Ganley B., Chowdhury G., Bhansali J., Daniels J.S., Gates K.S. Bioorg. Med. Chem. 9:2001;2395
12. Brown J.M. Br. J. Cancer. 67:1993;1163
13. Monge A., Palop J.A., López de Ceráin A., Senador V., Martínez-Crespo F.J., Sainz Y., Narro S., García E., de Miguel C., González M., Hamilton E., Barker A.J., Clarke E.D., Greenhow D.T. J. Med. Chem. 38(10):1995;1786
14. Monge A., Martínez-Crespo F.J., López de Ceráin A., Palop J.A., Narro S., Senador V., Marín A., Sainz Y., González M., Hamilton E., Barker A.J. J. Med. Chem. 38(22):1995;4488
15. Monge A., Palop J.A., González M., Martínez-Crespo F.J., López de Ceráin A., Sainz Y., Narro S., Barrer A.J., Hamilton E. J. Heterocycl. Chem. 32:1995;1213
16. Martínez-Crespo F.J., Palop J.A., Sainz Y., Narro S., Senador V., González M., López de Ceráin A., Monge A., Hamilton E., Barker A.J. J. Heterocycl. Chem. 33:1996;1671
17. Ortega M.A., Sainz Y., Montoya M.E., Jaso A., Zarranz B., Aldana I., Monge A. Arzneim. Forsch./Drug Res. 52:2002;113
18. Cheeseman G.W.H. Cookson R.F. Condensed Pyrazines. 1979;35 J. Wiley and Sons, New York
19. Ortega M.A., Morancho M.J., Martínez-Crespo F.J., Sainz Y., Montoya M.E., Cerain A.L., Monge A. Eur. J. Med. Chem. 35:2000;21
20. Boyd M.R. Status of the NCI Preclinical Antitumor Drug Discovery Screen. Principles and Practice of Oncology. Vol. 3:1989;1-12
21. Monks A., Scudiero D., Skehaan P., Shoemaker R., Paull K., Vistica D., Hose C., Langley J., Cronise P., Vaigro-Wolff A., Gray-Goodrich M., Campbell H., Mayo J., Boyd M.R. J. Natl. Cancer Inst. 83:1991;757
22. Biotechniques. 21(5):1996;780
23. Plowman J., Dykes D.J., Hollingshead M., Simpson-Herren L., Alley M.C. Human Tumor Xenograft Models in NCI Drug Development. Teicher B. Anticancer Drug Development Guide: Preclinical Screening, Clinical Trials and Approval. 1997;101-125 Humana, Totowa, NJ