Synthesis and antimalarial activity of new 3-arylquinoxaline-2-carbonitrile derivatives

Arzneimittel-Forschung/Drug Research

Volumn 55, Issue 12, 2005, Pages 754-761

  Zarranz, Belén ^a   Jaso, Andrés ^a   Aldana, Ignacio ^a   Monge, Antonio ^a   Maurel, Séverine ^b   Deharo, Eric ^b   Jullian, Valérie ^b   Sauvain, Michel ^b  

^a UNIVERSITY OF NAVARRA   (Spain)

^b UMR 152 IRD Universite Paul Sabatier   (France)

Author keywords

Antimalarial agents; Quinoxaline carbonitrile derivatives, in vitro and in vivo studies, synthesis; Hernatin

Indexed keywords

3 (4 CHLOROPHENYL)QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 3 (4 METHYLPHENYL)QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 3 PHENYLQUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 3 [(4 METHOXYCARBONYL)PHENYL]QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 6,7 DICHLORO 3 (4 METHYLPHENYL)QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 6,7 DICHLORO 3 PHENYLQUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 6,7 DICHLORO 3 [(4 METHOXYCARBONYL)PHENYL]QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 6,7 DIFLUORO 3 (4 METHYL)PHENYLQUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 6,7 DIFLUORO 3 (4 METHYLPHENYL)QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 6,7 DIFLUORO 3 PHENYLQUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 6,7 DIFLUORO 3 [(4 METHOXYCARBONYL)PHENYL]QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 6,7 DIMETHYL 3 (4 CHLOROPHENYL)QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 6,7 DIMETHYL 3 (4 METHYLPHENYL)QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 6,7 DIMETHYL 3 PHENYLQUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 6,7 DIMETHYL 3 [(4 METHOXYCARBONYL)PHENYL]QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 7 CHLORO 3 (4 METHYLPHENYL)QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 7 CHLORO 3 PHENYLQUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 7 CHLORO 3 [(4 METHOXYCARBONYL)PHENYL]QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 7 DICHLORO 3 (4 METHYLPHENYL)QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 7 METHOXY 3 (4 CHLOROPHENYL)QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 7 METHOXY 3 (4 METHYLPHENYL)QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 7 METHOXY 3 PHENYLQUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 7 METHOXY 3 [(4 METHOXYCARBONYL)PHENYL]QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 7 METHYL 3 (4 CHLOROPHENYL)QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 7 METHYL 3 (4 METHYLPHENYL)QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 7 METHYL 3 PHENYLQUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; 7 METHYL 3 [(4 METHOXYCARBONYL)PHENYL]QUINOXALINE 2 CARBONITRILE 1,4 DIOXIDE; CYANIDE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; ERYTHROCYTE; FEMALE; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PLASMODIUM FALCIPARUM;

EID: 29744447563     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1296926     Document Type: Article

References (36)

1. Mishra, S. K., Satpathy, S. K., Mohanty, S., Survey of malaria treatment and deaths. Bull. WHO 77, 1020 (1999).
2. Bloland, P. B., Drug Resistance in Malaria; WHO, Geneva, Switzerland (2001)
3. WHO, Malaria (Fact sheet No. 94), Geneva, Switzerland (1998)
4. Krogstad, D. J., Gluzman, I. Y., Kyle, D. E. et al., Efflux of chloroquine from Plasmodium falciparum: mechanism of chloroquine resistance. Science. 238, 1283 (1987)
5. Sullivan, D. J., Gluzman, Jr., I., Russell, Y. et al., On the molecular mechanism of chloroquine's antimalarial action. Proc. Natl. Acad. Sci. USA 93, 11865 (1996)
6. White, N. J., Antimalarial drug resistance: the pace quickens. J. Antimicrob. Chemother. 30, 571 (1992)
7. Van Es, H. H., Skamene, G. E., Schurr, E., Chemotherapy of malaria: a battle against all odds? Clin. Invest. Med. 16, 285 (1993)
8. Cheeseman, G. W. H., Cookson, R. F., In The Chemistry of Heterocyclic Compounds, 2nd ed., A. Weissberger, E. C. Taylor (eds.), pp. 1-27, 35-38, J. Wiley & Sons, New York (1979)
9. Porter, A. E. A., In: Comprehensive Heterocyclic Chemistry, vol. 3, A. R. Katrizky, C. W. Rees (eds.), pp. 157-197, Pergamon Press, New York, (1984)
10. Aguirre, G., Cerecetto, H., Di Maio, R. et al., Quinoxaline N,N′-dioxide derivatives and related compounds as growth inhibitors of Trypanosoma cruzi. Structure-activity relationships. Bioorg. Med. Chem. Lett. 14, 3835 (2004)
11. Jaso, A., Zarranz, B., Aldana, I. et al., Synthesis of New Quinoxaline-2-carboxylate 1,4-Dioxide Derivatives as Anti-Mycobacterium tuberculosis Agents. J. Med. Chem. 48, 6, 2019 (2005)
12. Carta, A., Paglietti, G., Rhbarnikookar, M. E. et al., Novel substituted quinoxaline 1,4-dioxides with in vitro antimycobacterial and anticandida activity. Eur. J. Med. Chem. 37, 355 (2002)
13. Sanna, P., Carta, A., Loriga, M. et al., Preparation and biological evaluation of 6/7-trifluoromethyl(nitro)-, 6,7-difluoro-3-alkyl (aryl)-substituted-quinoxalin-2-ones. Part 3. Farmaco 54, 169 (1999)
14. Dirlam, J. P., Presslitz, J. E., Williams, B. J., Synthesis and antibacterial activity of some 3-[(alkylthio)methyl]quinoxaline 1-oxide derivatives. J. Med. Chem. 26, 1122 (1983)
15. Guillon, J., Grellier, P., Labaied, M. et al., Synthesis, antimalarial activity, and molecular modeling of new pyrrolo[1,2a] quinoxalines, bispyrrolo[1,2-a]quinoxalines, bispyrido [3,2-e] pyrrolo[1,2-a]pyrazines, and bispyrrolo[1,2-a]thieno [3,2-e] pyrazines. J. Med. Chem. 47, 1997 (2004)
16. Aldana, I., Ortega, M. A., Jaso, A. et al. Anti-malarial activity of some 7-chloro-2-quinoxalinecarbonitrile-1,4-di-N-oxide derivatives. Pharmazie. 58, 68 (2003)
17. Ortega, M. A., Sainz, Y., Montoya, M. E. et al., Anti-Mycobacterium tuberculosis agents derived from quinoxaline-2-carbonitrile and quinoxaline-2-carbonitrile 1,4-di-N-oxide. Arzneim.-Forsch./Drug Res. 52, 113 (2002)
18. Haddadin, M., Issidorides, C., The Beirut reaction. Heterocycles 35, 1525 (1993)
19. Cheeseman, G. W. H., Cookson, R. F., In: Condensed Pyrazines, p. 35, J. Wiley & Sons, New York (1979)
20. Ortega, M. A., Morancho, M. J, Martínez-Crespo, F. J. et al., New quinoxalinecarbonitrile 1,4-di-N-oxide derivatives as hypoxic-cytotoxic agents. Eur. J. Med. Chem. 35, 21 (2000)
21. Haddadin, M. J., Zhar, G. E., Rawdah, J. N. et al., Deoxygenation of quinoxaline N-oxides and related compounds. Tetrahedron 30, 659 (1974)
22. Kurosawa, Y., Takada, A., Kim, H. S., Progress in the chemistry of quinoxaline N-oxides and N,N′-dioxides. J. Heterocyclic Chem. 32, 1085 (1995)
23. Makler, M. T., Hinrichs, D. J., Measurement of the lactate dehydrogenase activity of Plasmodium falciparum as an assessment of parasitemia. Am. J. Trop. Med. Hyg. 48, 205 (1993)
24. Delhaes, B. J., Lazaro, J. E., Gay, F. et al., The microculture tetrazolium assay (MTA): another colorimetric method of testing Plasmodium falciparum chemosensitivity. Ann. Trop. Med. Parasitol. 93, 31 (1999)
25. Parzy, D., Pradines, B., Keundjian, A. et al., Evaluation des résistances de Plasmodium falciparum aux antimalariques. Med, Trop. 55, 211 (1995)
26. Trager, W., Jensen, J. B., Human malaria parasites in continuous culture. Science 193, 673 (1976)
27. Tabbi, G., Cassino, C., Cavigiolio, G. et al., Water stability and cytotoxic activity relationship of a series of ferrocenium derivatives. ESR insights on the radical production during the degradation process. J. Med. Chem. 45, 5786 (2002)
28. Egan, T. J., Ross, D. C., Adams, P. A., Quinoline antimalarial drugs inhibit spontaneous formation of β-haematin (malaria pigment). FEBS Lett. 352, 54 (1994)
29. Hawley, S. R., Bray, P. G., Mungthin, M. et al., Relationship between Antimalarial Drug Activity, Accumulation, and Inhibition of Heme Polymerization in Plasmodium falciparum In Vitro. Antimicrob. Agents Chemother. 42, 682 (1998)
30. Dorn, A., Vippagunta, S. R., Matile, H. et al., An assesement of Drug-Haematin Binding as a Mechanism for Inhibition of Haematin Polymerisation by Quinoline Antimalarials. Biochem. Pharmacol. 55, 727 (1998)
31. Kurosawa, Y., Dorn, A., Kitsuji-Shirane, M. et al., Hematin Polymerization Assay as a High-Throughput Screen for Identification of New Antimalarial Pharmacophores. Antimicrob. Agents Chemother. 44, 2638 (2000)
32. Baelmans, R., Deharo, E., Muñoz, V. et. al., Experimental conditions for testing the inhibitory activity of chloroquine on the formation of β-hematin. Exp. Parasitol. 96, 243 (2000)
33. Baelmans, R., Deharo, E., Bourdy, G. et al., A search for natural bioactive compounds in Bolivia through a multidisciplinary approach. Part IV. Is a new haem polymerisation inhibition test pertinent for the detection of antimalarial natural products? J. Ethnopharmacol. 73, 271 (2000)
34. Deharo, E., García, R. N., Oporto, P. et al., A non-radiolabelled ferriprotoporphyrin IX biomineralisation inhibition test for the high throughput screening of antimalarial compounds. Exp. Parasitol. 100, 252 (2002)
35. Peters, W., Chemotherapy and drug resistance in malaria, 2nd ed., Academic Press, London (1980)
36. Wright, A. D., König, G. M., Angerhofer, C. K. et al., Antimalarial Activity: The search for Marine-Derived Natural Products with Selective Antimalarial Activity. J. Nat. Prod. 59, 710 (1996)