Unexpected reduction of ethyl 3-phenylquinoxaline-2-carboxylate 1,4-Di-N-oxide derivatives by amines

Molecules

Volumn 13, Issue 1, 2008, Pages 78-85

  Lima, Lidia M ^a,b   Vicente, Esther ^a   Solano, Beatriz ^a   Pérez Silanes, Silvia ^a   Aldana, Ignacio ^a   Monge, Antonio ^a  

^a UNIVERSITY OF NAVARRA   (Spain)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Amines; Carboxylate; Quinoxaline N oxides; Reduction

Indexed keywords

AMINE; AMINE OXIDE; ETHYL 3 PHENYLQUINOXALINE 2 CARBOXYLATE 1,4 DI N OXIDE; ETHYL 3-PHENYLQUINOXALINE-2- CARBOXYLATE 1,4-DI-N-OXIDE; OXIDE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMISTRY; CONFERENCE PAPER; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION;

AMINES; CYCLIC N-OXIDES; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; OXIDES; QUINOXALINES;

EID: 38949122494     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13010078     Document Type: Conference Paper

References (37)

1. Dirlam, J. P.; Presslitz, J. E. Synthesis and antibacterial activity of isomeric 6 and 7-acetyl-3-methyl-2-quinoxalinecarboxamide 1,4-dioxides. J. Med. Chem. 1978, 21, 483-485.
2. Dirlam, J. P.; Czuba, L. J.; Dominy, B. W.; James, R. B.; Pezzullo, R. M.; Presslitz, J. E.; Windisch, W. W. Synthesis and antibacterial activity of 1-hydroxy-1-methyl-1,3-dihydrofuro[3,4-b]quinoxaline 4,9-dioxide and related compounds. J. Med. Chem. 1979, 22, 1118-1121.
3. Monge, A.; Martinez-Crespo, F. J.; De Cerain, A. L.; Palop, J. A.; Narro, S.; Senador, V.; Marin, A.; Sainz, Y.; Gonzalez, M.; Hamilton, E.; Barker, A. J. Hypoxia-selective agents derived from 2-quinoxalinecarbonitrile 1,4-di-N-oxides. 2. J. Med. Chem. 1995, 38, 4488-4494.
4. Monge, A.; Palop, J. A.; De Cerain, A. L.; Senador, V.; Martinez-Crespo, F. J.; Sainz, Y.; Narro, S.; Garcia, E.; De Miguel, C.; Gonzalez, M.; Hamilton, E.; Barker, A. J.; Clarke, E. D.; Greenhow, D. T. Hypoxia-selective agents derived from quinoxaline 1,4-di-N-oxides. J. Med. Chem. 1995, 38, 1786-1792.
5. Montoya, M. E.; Sainz, Y.; Ortega, M. A.; De Cerain, A. L.; Monge, A. Synthesis and antituberculosis activity of some new 2-quinoxalinecarbonitriles. Farmaco 1998, 53, 570-573.
6. Ortega, M. A.; Sainz, Y.; Montoya, M. E.; De Cerain, A. L.; Monge, A. Synthesis and antituberculosis activity of new 2-quinoxalinecarbonitrile 1,4-di-N-oxides. Pharmazie 1999, 54, 24-25.
7. Sainz, Y.; Montoya, M. E.; Martinez-Crespo, F. J.; Ortega, M. A.; de Cerain, A. L.; Monge, A. New quinoxaline 1,4-di-N-oxides for treatment of tuberculosis. Arzneim.-Forsch. 1999, 49, 55-59.
8. Ortega, M. A.; Morancho, M. J.; Martinez-Crespo, F. J.; Sainz, Y.; Montoya, M. E.; de Cerain, A. L.; Monge, A. New quinoxalinecarbonitrile 1,4-di-N-oxide derivatives as hypoxic-cytotoxic agents. Eur. J. Med. Chem. 2000, 35, 21-30.
9. Ortega, M. A.; Montoya, M. E.; Jaso, A.; Zarranz, B.; Tirapu, I.; Aldana, I.; Monge, A. Antimycobacterial activity of new quinoxaline-2-carbonitrile and quinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives. Pharmazie 2001, 56, 205-207.
10. Carta, A.; Paglietti, G.; Rahbar Nikookar, M. E.; Sanna, P.; Sechi, L.; Zanetti, S. Novel substituted quinoxaline 1,4-dioxides with in vitro antimycobacterial and anticandida activity. Eur. J. Med. Chem. 2002, 37, 355-366.
11. Ortega, M. A.; Sainz, Y.; Montoya, M. E.; Jaso, A.; Zarranz, B.; Aldana, I.; Monge, A. Anti-Mycobacterium tuberculosis agents derived from quinoxaline-2-carbonitrile and quinoxaline-2-carbonitrile 1,4-di-N-oxide. Arzneim.-Forsch. 2002, 52, 113-119.
12. Aldana, I.; Ortega, M. A.; Jaso, A.; Zarranz, B.; Oporto, P.; Gimenez, A.; Monge, A.; Deharo, E. Anti-malarial activity of some 7-chloro-2- quinoxalinecarbonitrile-1,4-di-N-oxide derivatives. Pharmazie 2003, 58, 68-69.
13. Jaso, A.; Zarranz, B.; Aldana, I.; Monge, A. Synthesis of new 2-acetyl and 2-benzoyl quinoxaline 1,4-di-N-oxide derivatives as anti-Mycobacterium tuberculosis agents. Eur. J. Med. Chem. 2003, 38, 791-800.
14. Zarranz, B.; Jaso, A.; Aldana, I.; Monge, A. Synthesis and antimycobacterial activity of new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives. Bioorg. Med. Chem. 2003, 11, 2149-2156.
15. Aguirre, G.; Cerecetto, H.; Di Maio, R.; Gonzalez, M.; Alfaro, M. E. M.; Jaso, A.; Zarranz, B.; Ortega, M. A.; Aldana, I.; Monge-Vega, A. Quinoxaline N,N′-dioxide derivatives and related compounds as growth inhibitors of Trypanosoma cruzi. Structure-activity relationships. Bioorg. Med. Chem. Lett. 2004, 14, 3835-3839.
16. Carta, A.; Loriga, M.; Paglietti, G.; Mattana, A.; Fiori, P. L.; Mollicotti, P.; Sechi, L.; Zanetti, S. Synthesis, anti-mycobacterial, anti-trichomonas and anti-candida in vitro activities of 2-substituted-6,7-difluoro-3-methylquinoxaline 1,4-dioxides. Eur. J. Med. Chem. 2004, 39, 195-203.
17. Kim, Y. B.; Kim, Y. H.; Park, J. Y.; Kim, S. K. Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues. Bioorg. Med. Chem. Lett. 2004, 14, 541-544.
18. Perez-Melero, C.; Maya, A. B.; del Rey, B.; Pelaez, R.; Caballero, E.; Medarde, M. A new family of quinoline and quinoxaline analogues of combretastatins. Bioorg. Med. Chem. Lett. 2004, 14, 3771-3774.
19. Singh, S. K.; Saibaba, V.; Ravikumar, V.; Rudrawar, S. V.; Daga, P.; Rao, C. S.; Akhila, V.; Hegde, P.; Rao, Y. K. Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors. Bioorg. Med. Chem. 2004, 12, 1881-1893.
20. Zarranz, B.; Jaso, A.; Aldana, I.; Monge, A. Synthesis and anticancer activity evaluation of new 2-alkylcarbonyl and 2-benzoyl-3-trifluoromethyl- quinoxaline 1,4-di-N-oxide derivatives. Bioorg. Med. Chem. 2004, 12, 3711-3721.
21. Carta, A.; Corona, P.; Loriga, M. Quinoxaline 1,4-dioxide: A versatile scaffold endowed with manifold activities. Curr. Med. Chem. 2005, 12, 2259-2272.
22. Jaso, A.; Zarranz, B.; Aldana, I.; Monge, A. Synthesis of new quinoxaline-2-carboxylate 1,4-dioxide derivatives as anti-Mycobacterium tuberculosis agents. J. Med. Chem. 2005, 48, 2019-2025.
23. 3 in acetone in the synthesis of quinoxaline 1,4-dioxide derivatives designed as antimalarial drug candidates. J. Heterocycl. Chem. 2005, 42, 1381-1385.
24. Zarranz, B.; Jaso, A.; Aldana, I.; Monge, A.; Maurel, S.; Deharo, E.; Jullian, V.; Sauvain, M. Synthesis and antimalarial activity of new 3-arylquinoxaline-2-carbonitrile derivatives. Arzneim.-Forsch. 2005, 55, 754-761.
25. 4-dioxide derivatives by complexation with vanadium. Bioorg. Med. Chem. 2006, 14, 5503-5509.
26. Zarranz, B.; Jaso, A.; Lima, L. M.; Aldana, I.; Monge, A.; Maurel, S.; Sauvain, M. Antiplasmodial activity of 3-trifluoromethyl-2-carbonylquinoxaline di-N-oxide derivatives. Braz. J. Pharm. Sci. 2006, 42, 357-361.
27. Burguete, A.; Pontiki, E.; Hadjipavlou-Litina, D.; Villar, R.; Vicente, E.; Solano, B.; Ancizu, S.; Perez-Silanes, S.; Aldana, I.; Monge, A. Synthesis and anti-inflammatory/antioxidant activities of some new ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives and of their 4,5-dihydro-(1H)-pyrazole analogues. Bioorg. Med. Chem. Lett. 2007, 17, 6439-6443.
28. Solano, B.; Junnotula, V.; Marín, A.; Villar, R.; Burguete, A.; Vicente, E.; Pérez-Silanes, S.; Aldana, I.; Monge, A.; Dutta, S.; Sarkar, U.; Gates, K. S. Synthesis and biological evaluation of new 2-arylcarbonyl-3-trifluoromethylquinoxaline 1,4-di-N-oxide derivatives and their reduced analogs. J. Med. Chem. 2007, 50, 5485-5492.
29. Marín, A.; Lima, L. M.; Solano, B.; Vicente, E.; Pérez-Silanes, S.; Maurel, S.; Sauvain, M.; Aldana, I.; Monge, A.; Deharo, E. Antiplasmodial structure-activity relationship of 3-trifluoro-methyl-2-arylcarbonylquinoxaline 1,4-di-N-oxide derivatives. Exp. Parasitol. 2008, 118, 25-31.
30. Vicente, E.; Charnaud, S.; Bongard, E.; Villar, R.; Burguete, A.; Solano, B.; Ancizu, S.; Pérez-Silanes, S.; Aldana, I.; Vivas, L.; Monge, A. Synthesis and antiplasmodial activity of 3-furyl and 3-thienylquinoxaline-2- carbonitrile 1,4-di-N-oxide derivatives. Molecules 2008, 13, 69-77.
31. Vicente, E.; Lima, L. M.; Bongard, E.; Charnaud, S.; Villar, R.; Solano, B.; Burguete, A.; Pérez-Silanes, S.; Aldana, I.; Vivas, L.; Monge, A. Synthesis and structure-activity relationship of 3-phenylquinoxaline 1,4-di-N-oxide derivatives as antimalarial agents. Eur. J. Med. Chem. 2008, doi: 10.1016/j.ejmech.2007.1011.1024. In Press.
32. Lima, L. M.; Barreiro, E. J. Bioisosterism: A useful strategy for molecular modification and drug design. Curr. Med. Chem. 2005, 12, 23-49.
33. Inbaraj, J. J.; Motten, A. G.; Chignell, C. F. Photochemical and photobiological studies of tirapazamine (SR 4233) and related quinoxaline 1,4-di-N-oxide analogues. Chem. Res. Toxicol. 2003, 16, 164-170.
34. Kuhn, L. P. Catalytic reduction with hydrazine. J. Am. Chem. Soc. 1951, 73, 1510-1512.
35. Abul-Hajj, Y. J. Stereo specific reduction of steroidal 4-ene-3-ols with hydrazine. J. Org. Chem. 1971, 36, 2730.
36. Kluge, A. F.; Maddox, M. L.; Lewis, G. S. Formation of quinoxaline monoxides from reaction of benzofurazan oxide with enones and C-13 NMR correlations of quinoxaline N-oxides. J. Org. Chem. 1980, 45, 1909-1914.
37. Haddadin, M. J.; Zahr, G. E.; Rawdah, T. N.; Chelhot, N. C.; Issidorides, C. H. Deoxygenation of quinoxaline N-oxides and related compounds. Tetrahedron 1974, 30, 659-666.