Design, synthesis and activity against Trypanosoma cruzi azaheterocyclic analogs of megazol

Medicinal Chemistry

Volumn 3, Issue 5, 2007, Pages 460-465

  Carvalho, A S ^a   Menna Barreto, R F S ^a   Romeiro, N C ^a   de Castro, S L ^a   Boechat, N ^a  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

Author keywords

Azaheterocyclic derivatives; Chagas disease; Chemotherapy; Megazol; Trypanosoma cruzi

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; 2 AMINO 5 (1 METHYL 5 NITRO 2 IMIDAZOLYL) 1,3,4 THIADIAZOLE; 5 (1 METHYL 4 AMINE 1H 5 IMIDAZOLYL) 1H 1,2,4 TRIAZOL 3 AMINE; 5 (1 METHYL 4 NITRO 1H 5 IMIDAZOLYL) 1,2,4 TRIAZOL 3 AMINE; 5 (1 METHYL 4 NITRO 1H 5 IMIDAZOLYL) 1,3,4 THIADIAZOL 2 AMINE; 5 (1 METHYL 5 NITRO 1H 2 IMIDAZOLYL) 1H 1,2,4 TRIAZOL 3 AMINE; 5 [N [3 (5 TRIFLUOROMETHYL) 1,3,4 THIADIAZOLYL]]AMINO 1 METHYL 4 NITROIMIDAZOLE; 5 [N [3 (5 TRIFLUOROMETHYL) 1H 1,2,4 TRIAZOLYL]]AMINO 1 METHYL 4 NITROIMIDAZOLE; 5 N (1 PYRAZOLYL) 1 METHYL 4 NITROIMIDAZOLE; ANTITRYPANOSOMAL AGENT; HETEROCYCLIC NITRO COMPOUND; THIADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIPROTOZOAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG DESIGN; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; THEORETICAL STUDY; TRYPANOSOMA CRUZI; TRYPOMASTIGOTE;

ANIMALS; AZA COMPOUNDS; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; THIADIAZOLES; TRYPANOSOMA CRUZI;

EID: 34648834201     PISSN: 15734064     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340607781745519     Document Type: Article

References (26)

1. Berkelhammer, G.; Asato, G. Science, 1968, 162, 1146.
2. De Castro, S.L.; Meirelles, M.N.L. Mem. Inst. Oswaldo Cruz. 1990, 85, 95.
3. Filardi, L.S.; Brener, Z. Ann. Trop. Med. Parasitol., 1982, 76, 293.
4. Enanga, B.; Ariyanayagam, M.R.; Stewart, M.L.; Barrett, M.P. Antimicrob. Agents Chemother., 2003, 47, 3368.
5. Boda, C.; Enanga, B.; Dumet, H.; Chauvière, G.; Labrousse, F.; Couquet, C.; Saivin, S.; Houin, G.; Périé, J.; Dumas, M.; Bouteille, B. Vet. Parasitol., 2004, 121, 213.
6. Coura, J.R.; De Castro, S.L. Mem. Inst. Oswaldo Cruz, 2002, 97, 3.
7. Viodé, C.; Bettache, N.; Cenas, N.; Krauth-Siegel, R.L.; Chauvière, G.; Bakalara, N.; Périé, J. Biochem. Pharmacol., 1999, 57, 549.
8. Turrens, J.F.; Watts Jr., B.P.; Zhong, L.; Docampo, R. Mol. Biochem. Parasitol., 1996, 82, 125.
9. Maya, J.D.; Bollo, S.; Nunez-Vergara, L.; Squella, J.A.; Reppeto, Y.; Morello, A.; Périé, J.; Chauvière, G. Biochem. Pharmacol., 2003, 65, 999.
10. Ferreira, R.C.; Ferreira, L.C. Mutat. Res., 1986, 171, 11.
11. Poli, P.; Mello, M.A.; Buschini, A.; Mortara, R.A.; Albuquerque C.N.; Silva, S.; Rossi, C.; Zucchi, T.M. Biochem. Pharmacol., 2002, 64, 1617.
12. Nesslany, F.A; Brugier, S.A; Mouriès, M.A.A; Le Curieux, F.A; Marzin, D. Mutat. Res., 2004, 560, 147.
13. Chauvière, G.; Bouteille, B.; Enanga, B.; Albuquerque, C.; Croft, S.L.; Dumas, M.; Périé, J. J. Med. Chem., 2003, 46, 427.
14. Carvalho, S.A.; Silva, E.F.; Santa-Rita, R.M.; De Castro, S.L.; Fraga, C.A.M. Bioorganic Med. Chem. Lett., 2004, 14, 5967.
15. Boechat, N.; Carvalho, A.S.; Fernandez-Ferreira, E.; Soares, R.O.; Souza, A.S.; Gibaldi, D.; Bozza, M.; Pinto, A.C. Cytobios, 2001, 105, 83.
16. Carvalho, A.S.; Gibaldi, D.; Pinto, A.C.; Bozza, M.; Boechat, N. Lett. Drug Des. Discovery, 2006, 3, 98-101.
17. Walsh J.S.; Wang, R.; Bagan, E.; Wang, C.C.; Wislocki, P.; Miwa, G.T. J. Med. Chem., 1987, 30, 150.
18. Albuquerque, C.N.; Périé, J. Rev. Bras. Ciências Farm., 1999, 35, 57.
19. Mukherjee, A.; Kumar, S.; Seth, M.; Bhaduri, A.P. Indian J. Chem., 1989, 283, 391.
20. Silva, L.H.P.; Nussenszweig, V. Folia Clin. Biol., 1953, 20, 191.
21. Menna-Barreto, R.F.S.; Henriques-Pons, A.; Pinto, A. V.; Morgado-Diaz, J.A.; Soares, M.J.; De Castro, S.L. J. Antimicrob. Chemother., 2005, 56, 1034.
22. (a) Chou, J.T.; Jurs, P. J. Chem. Inf. Comput. Sci., 1979, 19, 172;
23. (b) Stanton, D.T.; Jurs, P.C. Anal. Chem., 1990, 62, 2323;
24. (c) Dewar, M.J.S.; Zoebisch, E.G.; Healy, E.F.; Stewart, J.J.P. J. Am. Chem. Soc., 1985, 107, 3902;
25. (d) SYBYL 6.8 Molecular Modeling Software, Tripos Associates Inc. St Louis, MO, 1999;
26. (e) Hyperchem Program Release 7, Evaluation copy for Windows; Hypercube, Inc., 2002.