New amide derivatives of quinoxaline 1,4-di-N-oxide with leishmanicidal and antiplasmodial activities

Molecules

Volumn 18, Issue 4, 2013, Pages 4718-4727

  Barea, Carlos ^a   Pabón, Adriana ^b,c   Pérez Silanes, Silvia ^a   Galiano, Silvia ^a   Gonzalez, German ^d   Monge, Antonio ^a   Deharo, Eric ^d,e   Aldana, Ignacio ^a  

^a UNIVERSITY OF NAVARRA   (Spain)

^b UNIVERSIDAD DE ANTIOQUIA   (Colombia)

^c UNIVERSIDAD DEL ATLÁNTICO   (Colombia)

^d UNIVERSITÉ DE TOULOUSE   (France)

^e INSTITUT DE RECHERCHE POUR LE DÉVELOPPEMENT   (France)

Author keywords

1,4 di N oxide; Antiplasmodial; Leishmanicidal; Quinoxaline

Indexed keywords

AMIDE; ANTIMALARIAL AGENT; ANTIPARASITIC AGENT; OXIDE; QUINOXALINE DERIVATIVE;

ANIMAL; ARTICLE; CERCOPITHECUS; CHEMISTRY; DRUG EFFECT; DRUG SENSITIVITY; HUMAN; IC 50; LEISHMANIA; LEISHMANIA INFANTUM; PLASMODIUM; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION; VERO CELL;

AMIDES; ANIMALS; ANTIMALARIALS; ANTIPARASITIC AGENTS; CERCOPITHECUS AETHIOPS; HUMANS; INHIBITORY CONCENTRATION 50; LEISHMANIA; LEISHMANIA INFANTUM; OXIDES; PARASITIC SENSITIVITY TESTS; PLASMODIUM; PLASMODIUM FALCIPARUM; QUINOXALINES; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS;

EID: 84876745365     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18044718     Document Type: Article

References (27)

1. WHO. World Malaria Report 2011. Available online: http://www.who.int/ malaria/ world-malaria-report-2011/en/index.html (accessed on 9 December 2012).
2. WHO. Leishmaniasis. Available online: http://www.who.int/entity/tdr/ diseases-topics/ leishmaniasis/en/ (accessed on 9 December 2012).
3. Amin, K.M.; Ismail, M.F.; Noaman, E.; Soliman, D.H.; Ammar, Y.A. New quinoxaline 1,4-di-Noxides. Part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides. Bioorg. Med. Chem. 2006, 14, 6917-6923.
4. Ganley, B.; Chowdhury, G.; Bhansali, J.; Daniels, J.S.; Gates, K.S. Redox-activated, hypoxia-selective DNA cleavage by quinoxaline 1,4-di-N-oxide. Bioorg. Med. Chem. 2001, 9, 2395-2401.
5. Torres, E.; Moreno, E.; Ancizu, S.; Barea, C.; Galiano, S.; Aldana, I.; Monge, A.; Pérez-Silanes, S. New 1,4-di-N-oxide-quinoxaline-2-ylmethylene isonicotinic acid hydrazide derivatives as anti-Mycobacterium tuberculosis agents. Bioorg. Med. Chem. Lett. 2011, 21, 3699-3703.
6. Moreno, E.; Ancizu, S.; Pérez-Silanes, S.; Torres, E.; Aldana, I.; Monge, A. Synthesis and antimycobacterial activity of new quinoxaline-2- carboxamide 1,4-di-N-oxide derivatives. Eur. J. Med. Chem. 2010, 45, 4418-4426.
7. Burguete, A.; Pontiki, E.; Hadjipavlou-Litina, D.; Ancizu, S.; Villar, R.; Solano, B.; Moreno, E.; Torres, E.; Perez-Silanes, S.; Aldana, I.; et al. Synthesis and biological evaluation of new quinoxaline derivatives as antioxidant and anti-inflammatory agents. Chem. Biol. Drug Des. 2011, 77, 255-267.
8. Patel, M.; Mc Hugh, R.J.; Cordova, B.C.; Klabe, R.M.; Erickson-Viitanen, S.; Trainor, G.L.; Rodgers, J.D. Synthesis and evaluation of quinoxalinones as HIV-1 reverse transcriptase inhibitors. Bioorg. Med. Chem. Lett. 2000, 10, 1729-1731.
9. Vicente, E.; Charnaud, S.; Bongard, E.; Villar, R.; Burguete, A.; Solano, B.; Ancizu, S.; Perez-Silanes, S.; Aldana, I.; 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.
10. Vicente, E.; Lima, L.M.; Bongard, E.; Charnaud, S.; Villar, R.; Solano, B.; Burguete, A.; Perez-Silanes, S.; Aldana, I.; Vivas, L.; et al. Synthesis and structure-activity relationship of 3-phenylquinoxaline 1,4-di-N-oxide derivatives as antimalarial agents. Eur. J. Med. Chem. 2008, 43, 1903-1910.
11. Burguete, A.; Estevez, Y.; Castillo, D.; Gonzalez, G.; Villar, R.; Solano, B.; Vicente, E.; Perez-Silanes, S.; Aldana, I.; Monge, A.; et al. Anti-leishmanial and structure-activity relationship of ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives. Memorias do Instituto Oswaldo Cruz 2008, 103, 778-780.
12. Urquiola, C.; Vieites, M.; Aguirre, G.; Marin, A.; Solano, B.; Arrambide, G.; Noblía, P.; Lavaggi, M.L.; Torre, M.H.; Gonzalez, M.; et al. Improving anti-trypanosomal activity of 3-aminoquinoxaline-2-carbonitrile N-1,N-4-dioxide derivatives by complexation with vanadium. Bioorg. Med. Chem. 2006, 14, 5503-5509.
13. Loriga, M.; Nuvole, A.; Paglietti, G.; Fadda, G.; Zanetti, S. 2-Phenyl-6(7)-R substituted quinoxalines N-oxides. Synthesis, structure elucidation and antimicrobial activity. Eur. J. Med. Chem. 1990, 25, 527-532.
14. Carta, A.; Corona, P.; Loriga, M. Quinoxaline 1,4-dioxide: A versatile scaffold endowed with manifold activities. Curr. Med. Chem. 2005, 12, 2559-2272.
15. Barea, C.; Pabón, A.; Castillo, D.; Zimic, M.; Quiliano, M.; Galiano S.; Pérez-Silanes, S.; Monge, A.; Deharo, E.; Aldana, I. New salicylamide and sulfonamide derivatives of quinoxaline 1,4-di-N-oxide with antileishmanial and antimalarial activities. Bioorg. Med. Chem. Lett. 2011, 21, 4498-4502.
16. Barea, C.; Pabón, A.; Galiano, S.; Pérez-Silanes, S.; González, G.; Deyssard, C.; Monge, A.; Deharo, E.; Aldana I. Antiplasmodial and leishmanicidal activities of 2-cyano-3-(4-phenylpiperazine- 1-carboxamido)quinoxaline 1,4-dioxide derivatives. Molecules 2012, 17, 9451-9461.
17. 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. Arzneimittelforschung 2002, 52, 113-119.
18. González, M.; Cerecetto, H. Benzofuroxan and Furoxan. Chemistry and Biology. In Topics in Heterocyclic Chemistry. Bioactive Heterocycles V; Springer: Berlin, Germany, 2007; Volume 10, pp. 265-308.
19. Ley, K.; Seng, F. Synthesis unter verwendung von benzofuroxan. Synthesis 1975, 7, 415-422.
20. Croft, S.L.; Sundar, S.; Fairlamb, A.H. Drug resistance in leishmaniasis. Clin. Microbiol. Rev. 2006, 19, 111-126.
21. Ancizu, S.; Moreno, E.; Torres, E.; Burguete, A.; Perez-Silanes, S.; Benitez, D.; Villar, R.; Solano, B.; Marin, A.; Aldana, I. Heterocyclic-2- carboxylic acid (3-cyano-1,4-di-Noxidequinoxalin- 2-yl)amide derivatives as hits for the development of neglected diseases drugs. Molecules 2009, 14, 2256-2272.
22. Cheeseman, G.W.H. Condensed Pyrazines; Cookson, R.F., Ed.; J. Wiley and Sons: New York, NY, USA, 1979; p. 35.
23. 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.
24. Desjardins, R.E.; Canfield, C.J.; Haynes, J.D.; Chulay, J.D. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob. Agents Chemother. 1979, 16, 710-718.
25. Sereno, D.; Lemesre, J.L. Use of an enzymatic micromethod to quantity amastigotes stage of Leishmania amazonensis in vitro. Parasitol. Res. 1997, 83, 401-403.
26. Cachet, N.; Hoakwie, F.; Bertani, S.; Bourdy, G.; Deharo, E.; Stien D.; Houel, E.; Gornitzka, H.; Fillaux, J.; Chevalley, S. Antimalarial activity of simalikalactone E, a new quassinoid from Quassia amara L. (Simaroubaceae). Antimicrob. Agents Chemother. 2009, 53, 4393-4398.
27. Muñoz, V.; Sauvain, M.; Mollinedo, P.; Callapa, J.; Rojas, I.; Gimenez, A.; Valentin, A.; Mallie, M. Antimalarial activity and cytotoxicity of (?)-roemrefidine isolated from the stem bark of Sparattanthelium amazonum. Planta Med. 1999, 65, 448-449.