Synthesis of new quinoxaline-2-carboxylate 1,4-dioxide derivatives as anti-Mycobacterium tuberculosis agents

Journal of Medicinal Chemistry

Volumn 48, Issue 6, 2005, Pages 2019-2025

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

^a UNIVERSITY OF NAVARRA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHOXYETHYL 6,7 DICHLORO 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; ALLYL 3,6,7 TRIMETHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; ALLYL 6,7 DICHLORO 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; BENZYL 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; BENZYL 3,6,7 TRIMETHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; BENZYL 3,7 DIMETHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; BENZYL 6,7 DICHLORO 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; BENZYL 6,7 DIFLUORO 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; BENZYL 7 CHLORO 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; BENZYL 7 METHOXY 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; ETHYL 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; ETHYL 3,6,7 TRIMETHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; ETHYL 3,7 DIMETHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; ETHYL 6,7 DICHLORO 3 (2 ETHOXY 2 OXOETHYL)QUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; ETHYL 6,7 DICHLORO 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; ETHYL 6,7 DIFLUORO 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; ETHYL 7 CHLORO 3 (2 ETHOXY 2 OXOETHYL)QUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; ETHYL 7 CHLORO 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; ETHYL 7 METHOXY 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; METHYL 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; METHYL 3,6,7 TRIMETHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; METHYL 3,7 DIMETHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; METHYL 6,7 DICHLORO 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; METHYL 6,7 DIFLUORO 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; METHYL 7 METHOXY 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; TERT BUTYL 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; TERT BUTYL 3,6,7 TRIMETHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; TERT BUTYL 6,7 DICHLORO 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; TERT BUTYL 7 CHLORO 3 METHYLQUINOXALINE 2 CARBOXYLATE 1,4 DIOXIDE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL GROWTH; CONTROLLED STUDY; DRUG ACTIVITY; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; GROWTH INHIBITION; IC 50; MINIMUM INHIBITORY CONCENTRATION; MULTIDRUG RESISTANCE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN;

ANIMALS; ANTITUBERCULAR AGENTS; CERCOPITHECUS AETHIOPS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; CYCLIC N-OXIDES; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; QUINOXALINES; SPECTROPHOTOMETRY, INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS;

EID: 15444370985     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049952w     Document Type: Article

References (28)

1. Snider, D. E.; Raviglione, M.; Kochi, A. In Global Burden of Tuberculosis. Tuberculosis: Patogenesis, Protection and Control; Bloom, B., Eds; ASM: Washington, DC, 1994; pp 3-4.
2. Enarson, D. A. Global disease and the role of international collaboration. Can. Med. Assoc. J. 2000, 162, 57-61.
3. Bishai, W. R.; Graham, N. M. H.; Harrington, S.; Pope, D. S.; Hooper, N.; Astemborski, J. Molecular and geographic patterns of tuberculosis transmission after 15 years of directly observed therapy. JAMA, J. Am. Med. Assoc. 1998, 280, 1679-1684.
4. OMS. WHO annual report on global TB control summary. Weekly Epidemiol. Rec. 2003, 78 (15), 121-128.
5. Bass, J. B., Jr.; Farer, L. S.; Hopewell, P. C.; O'Brien, R.; Jacobs, R. F.; Ruben, F.; Snider, D. E., Jr.; Thornton, G. Treatment of tuberculosis and tuberculosis infection in adults and children. American Thoracic Society and The Centers for Disease Control and Prevention. Am. J. Respir. Crit. Care Med. 1994, 149, 1359-1374.
6. Pathak, A. K.; Pathak, V.; Seitz, L.; Maddry, J. A.; Gurcha, S. S.; Besra, G. S.; Suling, W. J.; Reynolds, R. C. Studies on (β,1-5) and (β,1-6) Linked Octyl Galf Disaccharides as Substrates for Mycobacterial Galactosyltransferase Activity. Bioorg. Med. Chem. 2001, 9, 3129-3143.
7. Cheeseman, G. W. H.; Cookson, R. F. In The Chemistry of Heterocyclic Compounds, 2nd ed.; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1979; pp 1-27, 35-38.
8. Porter, A. E. A. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984; Vol. 3, pp 157-197.
9. Carta, A.; Paglietti, G.; Rhbarnikookar, 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.
10. Sanna, P.; Carta, A.; Loriga, M.; Zanetti, S.; Sechi, L. Synthesis of 3,6,7-substituted-quinoxalin-2-ones for evaluation of antimicrobial and anticancer activity. Part 2. Farmaco 1999, 54, 169-177.
11. 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. 1983, 26, 1122-1126.
12. Takabatake, T.; Takabatake, Y.; Miyazawa, T.; Hasegawa, M. Synthesis and antibacterial properties of quinoxaline 1,4-dioxide derivatives. Yakugaku Zasshi 1996, 116, 491-496.
13. Novacek, L. The antibacterial, quinoxaline 1,4-dioxide. Cesk. Farm. 1981, 30, 26-32.
14. el-Hawash, S. A.; Habib, N. S.; Fanaki, N. H. Quinoxaline derivatives. Part II: Synthesis and antimicrobial testing of 1,2,4-triazolo[4,3-α] quinoxaline 1,2,4-triazino[4,3-α]quinoxalines and 2-pyrazolylquinoxalines. Pharmazie 1999, 54, 808-813.
15. Badran, M. M.; Abouzid, K. A.; Hussein, M. H. Synthesis of certain substituted quinoxalines as antimicrobial agents (Part II). Arch Pharmacal. Res. 2003, 26, 107-113.
16. Hutchinson, M. J.; Young, P. Y.; Hewitt, S. A.; Faulkner, D.; Kennedy, D. G. Development and validation of an improved method for confirmation of the carbadox metabolite, quinoxaline-2-carboxylic acid, in porcine liver using LC-electrospray MS-MS according to revised EU criteria for veterinary drug residue analysis. Analyst 2002, 127, 342-346.
17. Dunlop, S. H.; McEwen, S. A.; Meek, A. H.; Friendship, R. A.; Clarke, R. C.; Black, W. D. Antimicrobial drug use and related management practices among Ontario swine producers. Can. Vet. J. 1998, 39, 87-96.
18. Yen, T. J.; Pnd, W. G. Effects of carbadox, copper, or Yucca shidigera extract on growth performance and visceral weight of young pigs. J Anim. Sci. 1993, 71, 2140-2146.
19. Monge, A.; Palop, J. A.; Lopez de Cerain, 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. Hypoxia-selective agents derived from 2-quinoxalinecarbonitrile 1,4-di-N-oxides. J. Med. Chem. 1995, 38, 1786-1792.
20. 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.
21. 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.
22. Montoya, M. E.; Sainz, Y.; Ortega, M. A.; Lopez de Cerain, A.; Monge, A. Synthesis and antituberculosis activity of some new 2-quinoxalinecarbonitriles. Farmaco 1998, 53, 570-573.
23. 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.
24. Ortega, M. A.; Morancho, M. J.; Martínez-Crespo, F. J.; Sainz, Y.; Montoya, M. E.; Lopez de Cerain, A.; Monge, A. New quinoxalinecarbonitrile 1,4-di-N-oxide derivatives as hypoxiccytotoxic agents. Eur. J. Med. Chem. 2000, 35, 21-30.
25. Takabatake, T.; Hasegawa, Y.; Hasegawa, H. The reactions of benzofuroxan with carbonyl compounds on the surface of solid catalyst. J. Heterocycl. Chem. 1993, 30, 1477-1479.
26. Collins, L. A.; Franzblau, S. G. Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents Chemother. 1997, 41, 1004-1009.
27. Skinner, P. S.; Furney, S. K.; Jacobs, M. R.; Klopman, G.; Ellner, J. J.; Orme, I. M. A bone marrow-derived murine macrophage model for evaluating efficacy of antimycobacterial drugs under relevant physiological conditions. Antimicrob. Agents Chemother. 1994, 38, 2557-2563.
28. Kelly, B. P.; Furney, S. K.; Jessen, M. T.; Orme, I. M. Low-dose aerosol infection model for testing drugs for efficacy against Mycobacterium tuberculosis. Antimicrob. Agents Chemother. 1996, 40, 2809-2812.