Synthesis and anti-Trypanosoma cruzi activity of derivatives from nor-lapachones and lapachones

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 9, 2008, Pages 5030-5038

  da Silva Júnior, Eufrânio N ^a,b   de Souza, Maria Cecília B V ^a   Fernandes, Michelle C ^c   Menna Barreto, Rubem F S ^c   Pinto, Maria do Carmo F R ^d   de Assis Lopes, Francisco ^d   de Simone, Carlos Alberto ^e   Andrade, Carlos Kleber Z ^b   Pinto, Antônio V ^d   Ferreira, Vitor F ^a   de Castro, Solange L ^c  

^a FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

^b UNIVERSITY OF BRASILIA   (Brazil)

^c INSTITUTO OSWALDO CRUZ   (Brazil)

^d FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^e FEDERAL UNIVERSITY OF ALAGOAS   (Brazil)

Author keywords

Chagas' disease; Chemotherapy; Lapachone; Naphthoquinones; Trypanosoma cruzi

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 2,2 DIMETHYL 3 HYDRO 4 OXANAPHTHO[2,3 B]FURANE 9 SPIRO 2' OXYRANE; 2,2 DIMETHYL 4 PHENYLAMINO 3,4 DIHYDRO 2H BENZO[G]CHROMENE 5,10 DIONE; 3 (3 FLUOROPHENYLAMINO) 2,2 DIMETHYL 2,3 DIHYDRONAPHTHO[1,2 B]FURAN 4,5 DIONE; 3 (4 BROMOPHENYLAMINO) 2,2 DIMETHYL 2,3 DIHYDRONAPHTHO[1,2 B]FURAN 4,5 DIONE; 3 (4 CHLOROPHENYLAMINO) 2,2 DIMETHYL 2,3 DIHYDRONAPHTHO[1,2 B]FURAN 4,5 DIONE; 3 (4 METHOXYPHENYLAMINO) 2,2 DIMETHYL 2,3 DIHYDRONAPHTHO[1,2 B]FURAN 4,5 DIONE; 3 (4 NITROPHENYLAMINO) 2,2 DIMETHYL 2,3 DIHYDRONAPHTHO[1,2 B]FURAN 4,5 DIONE; 3 AZIDO 2,2 DIMETHYL 2,3 DIHYDRONAPHTHO[2,3 B]FURAN 4,9 DIONE; ANTITRYPANOSOMAL AGENT; AZIDE; BENZNIDAZOLE; FUNCTIONAL GROUP;

ANTIPROTOZOAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HYBRID; IC 50; INFRARED RADIATION; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; TRYPANOSOMA CRUZI; TRYPOMASTIGOTE; X RAY CRYSTALLOGRAPHY;

ANIMALS; ANTIPROTOZOAL AGENTS; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NAPHTHOQUINONES; PARASITIC SENSITIVITY TESTS; STEREOISOMERISM; TRYPANOSOMA CRUZI;

IONE; TRYPANOSOMA CRUZI;

EID: 43049170148     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.03.032     Document Type: Article

References (35)

1. Moncayo A., and Ortiz-Yanine M.I. Ann. Trop. Med. Parasitol. 100 (2006) 663-677
2. Schmunis G.A. Mem. Inst. Oswaldo Cruz 102 Suppl. I (2007) 75-85
3. Teixeira A.R., Nitz N., Guimaro M.C., Gomes C., and Santos-Buch C.A. Postgrad. Med. J. 82 (2006) 788-798
4. Coura J.R. Mem. Inst. Oswaldo Cruz 102 Suppl. I (2007) 113-122
5. Coura J.R., and De Castro S.L. Mem. Inst. Oswaldo Cruz 97 (2002) 3-24
6. Jannin J., and Villa L. Mem. Inst. Oswaldo Cruz 102 Suppl. I (2007) 95-97
7. Pinto A.V., Menna-Barreto R.F.S., and De Castro S.L. In: Govil J.N. (Ed). Recent Progress in Medicinal Plants. Phytomedicines Vol. 16 (2006), Studium Press, Houston, Texas 112-127
8. Viegas Jr. C., Danuello A.C., Bolzani V.S., Barreiro E.J., and Fraga C.A.M. Curr. Med. Chem. 14 (2007) 1829-1852;
9. Pinto A.V., Neves-Pinto C., Pinto M.C.F.R., Santa-Rita R.M., Pezzella C., and De Castro S.L. Arzneim-Forsch 47 (1997) 74-79
10. Neves-Pinto C., Dantas A.P., Moura K.C.G., Emery F.S., Polequevitch P.F., Pinto M.C.F.R., De Castro S.L., and Pinto A.V. Arzneim-Forsch 50 II (2000) 1120-1128
11. Neves-Pinto C., Malta V.R., Pinto M.C.F.R., Santos R.H., De Castro S.L., and Pinto A.V. J. Med. Chem. 45 (2002) 2112-2115
12. Moura K.C., Emery F.S., Neves-Pinto C., Pinto M.C.F.R., Dantas A.P., Salomão K., De Castro S.L., and Pinto A.V. J. Braz. Chem. Soc. 12 (2001) 325-338
13. Moura K.C., Salomão K., Menna-Barreto R.F.S., Emery F.S., Pinto M.C.F.R., Pinto A.V., and De Castro S.L. Eur. J. Med. Chem. 39 (2004) 639-645
14. Menna-Barreto R.F.S., Henriques-Pons A., Pinto A.V., Morgado-Diaz J.A., Soares M.J., and De Castro S.L. J. Antimicrob. Chemother. 56 (2005) 1034-1041
15. Menna-Barreto R.F.S., Corrêa J.R., Pinto A.V., Soares M.J., and De Castro S.L. Parasitol. Res. 101 (2007) 895-905
16. Silva R.S.F., Costa E.M., Trindade U.L.T., Teixeira D.V., Pinto M.C.F.R., Santos G.L., Malta V.R.S., De Simone C.A., Pinto A.V., and De Castro S.L. Eur. J. Med. Chem. 41 (2006) 526-530
17. Ferreira V.F., Jorqueira A., Souza A.M.T., Silva M.N., Souza M.C.B.V., Gouvêia R.M., Rodrigues C.R., Pinto A.V., Castro H.C., Santos D.O., Araújo H.P., and Bourguignon S.C. Bioorg. Med. Chem. 14 (2006) 5459-5466
18. Jorqueira A., Gouvêa R.M., Ferreira V.F., da Silva M.N., de Souza M.C.B.V., Zuma A.A., Cavalcanti D.F.B., Araújo H.P., Santos D.O., and Bourguignon S.C. Parasitol. Res. 99 (2006) 429-433
19. da Silva Júnior E.N., Souza M.C.B.V., Pinto A.V., Pinto M.C.F.R., Ferreira V.F., Menna-Barreto R.F.S., Silva R.S.F., Teixeira D.V., de Simone C.A., and De Castro S.L. Eur. J. Med. Chem. (2007) 10.1016/j.ejmech.2007.10.015 Oct 22 Epub ahead of print
20. Fieser L.F., and Fieser M. J. Am. Chem. Soc. 70 (1948) 3215-3222
21. Pinto A.V., Pinto M.C.F.R., and de Oliveira C.G.T. An. Acad. Bras. Cienc. 54 (1982) 107-114
22. Pinto A.V., Pinto M.C.R., Gilbert B., Pellegrino J., and Mello R.T. Trans. R. Soc. Trop. Med. Hyg. 71 (1977) 133-135
23. Ferreira V.F., Pinto A.V., Pinto M.C.R.F., Silva M.N., Skakle J.M.S., Souza M.C.B.V., and Wardell S.M.S.V. Acta Crystallogr. C58 (2002) 560-562
24. Silva M.N., de Souza M.C.B.V., Ferreira V.F., Pinto A.V., Pinto M.C.R.F., Wardell S.M.S.V., and Wardell J.L. Arkivoc 10 (2003) 156
25. da Silva. Júnior E.N., Souza M.C.B.V., Pinto A.V., Pinto M.C.F.R., Goulart M.O.F., Barros F.W.A., Pessoa C., Costa-Lotufo L., Montenegro R.C., Moraes M.O., and Ferreira V.F. Bioorg. Med. Chem. 15 (2007) 7035-7041
26. Allen F.H. Acta Cryst. B58 (2002) 380-388
27. Cremer D., and Pople J.A. J. Am. Chem. Soc. 97 (1975) 1354-1358
28. Pereira E.M., Machado T.B., Leal I.C.R., Jesus D.M., Damaso C.R.A., Pinto A.V., Giambiagi-deMarval M., Kuste R.M., and dos Santos K.R.N. Ann. Clin. Microbiol. Antimicrob. 5 (2006) 1-7
29. Arenas P. J. Ethnopharmacol. 21 (1987) 279-295
30. Silva L.H.P., and Nussenszweig V. Folia Clin. Biol. 20 (1953) 191-208
31. Enraf-Nonius, COLLECT. Nonius BV, Delft, The Netherlands, 2000.
32. Sheldrick G.M. SHELXS-97 and SHELXL-97 (1997), Univ. of Göttingen, Germany
33. Farrugia L.J.J. App. Cryst. 30 (1997) 565-566
34. Farrugia L.J.J. App. Cryst. 32 (1999) 837-838
35. Otwinowski Z., and Minor W.H.K.L. In: Carter C.W., and Sweet R.M. (Eds). Methods in Enzymology (1997), Academic Press, New York 307-326