Nova rota de sîntese do megazol [1-metil-2-(5-amino-1,3,4-tiadiazol-2-il)-5-nitroimidazol], urn antiparasitârio ativo contra o Trypanosoma cruzi

Revista Brasileira de Ciencias Farmaceuticas/Brazilian Journal of Pharmaceutical Sciences

Volumn 35, Issue 1, 1999, Pages 57-64

  Albuquerque, Cristina Northfleet ^a,b   Perie, J J ^a,b  

^a Université Paul Sabatier   (France)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Chagas'disease; Megazol; Nitroimidazole; Synthesis; Trypanosoma cruzi

Indexed keywords

EID: 0346246122     PISSN: 15169332     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. ALBRIGHT, J. D., SHEPHERD, R. G. Reactions of 1,2dimethyl-5-nitroimidazole, novel methods of conversion of the 2-methyl group to a nitrile. J. Hetemcycl. Chem., Provo, v.10, p. 899-907, 1973.
2. ALBUQUERQUE, C. N. Synthèse et études physicochimique d'analogues du Megazol, antiparasitaire du type nitro-imidazole; études de leur mode d'action. Toulouse, 1995. 207p. [Tese de Doutoramento, Université Paul Sabatier, Franca].
3. ANDRADE, S. G., MAGALHÄES, J. B., PONTES, A. L. Evaluation of chemotherapy with benznidazole and nifurtimox in mice infected with Trypanosoma cruzi strains of different types. Bull. WHO, Geneva, v.63, n.4, p.721-6, 1985.
4. BERKELHAMMER, G., ASATO, G. 2-amino-5(l -methyl-5nitro-2-imidazolyl)-1,3,4-thiadiazole: a new antimicrobial agent. Science, Washington, v. 162, p. 1146, 1968.
5. BRENER, Z. Present status of chemotherapy and chemoprophylaxis of human trypanosomiasis in the western hemisphere. Pharmacol. Ther., Oxford, v.7, p.71-90, 1979.
6. BURDEN, E. J., RACETTE, E. 2-amino-5-( l -methyl-5-nitro2-imidazolyl)-1,3,4-thiadiazole, a new antimicrobial agent. IX. Action against hemoflagellate infections in laboratory animals. Antimicrob. Agents Chemother., Washington, v.7, p.545-7, 1968.
7. CRUZ, F. S., V1LLALTA, F., MUN1Z, R. F. A. Mechanism of nifurtimox toxicity in different forms of Trypanosoma cnizi. Biochem. Pharmacol., London, v.30, n. 14, p. 194751,1981.
8. DE CASTRO, S. L. The challenge of Chagas' Disease chemotherapy: an update of drugs assayed against Trypanosoma cnizi. Acta Tropica, Basel, v.53, p.83-98, 1993.
9. DIAS, J.C.P., JATENE, A.D. Doenc̃a de Chagas no Brasil Situacäo atual e perspectivas. Rev. Soc. Bras. Med. Tropical, Rio de Janeiro, v.25, supl.3, p.6-8, 1992.
10. DO CAMPO, R., MARR, J.J. Chemotherapy of Chagas' disease: a perspective of current therapy and considerations for future research. Rev. Infec. Dis., Chicago, v.8, n.6,p.884, 1986.
11. FILARDI, L. S. BRENER, Z. A nitroimidazole-thiadiazole derivative with curative action in experimental Trypanosoma cnizi infections. Ann. Trop. Med. Parasitai, Liverpool, v.76, p.293-7,1982.
12. GRUNBERG, E., TITSWORTH, E. H. Chemotherapeutic properties of heterocyclic compounds: monocyclic compounds with five-membered rings. Ann. Rev. Microbiol, Palo Alto, v.27, p.317-46, 1973.
13. IDDON, B., LIM, B.L. Reactions of 1,2-dimethylimidazole, particularly its metallation. J. Chem. Soc. Perkin Trans. I, London, p.271-6,1983a.
14. IDDON, B., LIM, B.L. Metal-halogen exchange reactions of mono- and poly-halogenoimidazoles. J. Chem. Soc. Perkin Trans. I, London, p.735-40, 1983b.
15. JOHNSON, S. T. 1-alkylation of 4,5-dicyanoimidazole by ortho esters. Synthesis, Stuttgart, p. 75-7, 1991.
16. KULKARNI, S. et al. Nucleophilic displacements of imidazoles. I. Oxygen, nitrogen and carbon nucleophiles. Aust. J. Chem., Melbourne, v.40, p.1399-402,1987.
17. NAIR, M. D., NAGARAJAN, K. Nitroimidazoles äs chemotherapeutic agent. Prog. Drug Res., Basel, v.27, p.163-252, 1983.
18. NEVES, D. P., MELO, A. L., GENARO, O., LINARDI, P. M. Parasitologia Humana. 9.ed. Sào Paulo: Atheneu, 1995,p.82-114.
19. MEO, M. ,VANELLE, P., BERNADINI, E., LÄGET, M., MALDONADO, J., JENTZER, O., CROZET, M. P. DUMÉNIL, G. Evaluation of the mutagenic and genotoxic activities of 48 nitroimidazoles and related imidazole derivatives by the AMES test and the SOS chromotest. Environ. Mol. Mutagen., New York, v. 19, p. 167-81,1992.
20. REMERS, W. A., GIBS, G. J., WEISS, M. J. Preparation of halomethyl-1,3,4-thiadiazole, conversion to 2-amino-5( 1 -methyl-5 -nitro-2-imidazolyl)-1,3,4-thiadiazole, an important antimicrobial agent. J. Heterocycl. Chem., Provo, v.6, n.6, p.835-40, 1969.
21. TSUHAKO, M. H. , ALVES, M. J. M. , COLLI, W. , BRENER, Z., AUGUSTO, O. Restricted bioreductive metabolism of a nitroimidazole-thiadiazole derivative with curative action in experimental Trypanosoma cnizi infections. Biochem. Pharmacol., London, v.38, p.4491-6, 1989.
22. TSUHAKO, M. H. Metabolismo redutivo dos tripanocidas megazol e nifurtimox. Sào Paulo, 1990. 84p. [Dissertac̃ào de mestrado, Universidade de Säo Paulo, IQ].
23. WALSH, J. S. et al. Structural alterations that differentially affect the mutagenic and antitrichomonal activities of 5nitroimidazoles. J. Med. Chem., Washington, v.30, p. 1506,1987.
24. WRITTEN, J. P., MATHEUS, D. P., MCCARTHY, J. R. [2(trimethylsilyl)ethoxy]methyl (SEM) as a novel and effective imidazole and fused aromatic imidazole protecting group. J. Org. Chem., Baltimore, v.51, p. 1891 2, 1986.
25. WORLD HEALTH ORGANIZATION - Control of Chagas' disease , Geneva, 1991. p.23-25. (Technical Report Series).
26. WINKELMANN, E., RAETHER, W., GREBERT, V., SINHARAY, A. Chemotherapeutically active nitro compounds. 5-nitroimidazoles(PartI).rze/m. Forsch./ DrugRes., Basel, v. 12, p.2251-63, 1977.