Imidazolidin-4-one peptidomimetic derivatives of primaquine: Synthesis and antimalarial activity

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 14, 2008, Pages 4150-4153

  Vale, Nuno ^a   Matos, Joana ^a   Gut, Jiri ^b   Nogueira, Fátima ^c   do Rosário, Virgílio ^c   Rosenthal, Philip J ^b   Moreira, Rui ^d   Gomes, Paula ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c INSTITUTO DE HIGIENE E MEDICINA TROPICAL   (Portugal)

^d RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

Author keywords

Antimalarial; Gametocytocidal; Imidazolidin 4 one; Malaria; Peptidomimetic; Primaquine

Indexed keywords

ANTIMALARIAL AGENT; CHLOROQUINE; IMIDAZOLIDIN 4 ONE DERIVATIVE; IMIDAZOLIDINE DERIVATIVE; PRIMAQUINE;

ACYLATION; ANIMAL TISSUE; ANTIMALARIAL ACTIVITY; ARTICLE; DRUG STABILITY; DRUG SYNTHESIS; MIDGUT; MOSQUITO; NONHUMAN; PARASITE TRANSMISSION; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIMALARIALS; CHROMATOGRAPHY, THIN LAYER; DRUG DESIGN; HUMANS; HYDROGEN-ION CONCENTRATION; IMIDAZOLES; INHIBITORY CONCENTRATION 50; MALARIA; MODELS, CHEMICAL; PEPTIDES; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; PRIMAQUINE; STRUCTURE-ACTIVITY RELATIONSHIP;

PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM;

EID: 47149096687     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.05.076     Document Type: Article

References (27)

1. Brueckner R.P., Ohrt C., Baird J.K., and Milhous W.K. 8-Aminoquinolines. In: Rosenthal P.J. (Ed). Antimalarial Chemotherapy (2001), Humana Press, Totowa 123
2. Mihaly G.W., Ward S.A., Edwards G., Orme M.L.E., and Breckenridge A.M. Br. J. Clin. Pharmacol. 17 (1984) 441
3. Baker J.K., Bedford J.A., Clark A.M., and McChesney J.D. Pharm. Res. 1 (1984) 98
4. Baker J.K., Yarber R.H., Nanayakkara N.P.D., McChesney J.D., Homo F., and Landau I. Pharm. Res. 7 (1990) 91
5. Constantino L., Paixão P., Moreira R., Portela M.J., Rosário V.E., and Iley J. J. Exp. Toxicol. Pathol. 51 (1999) 299
6. Umbreit J. Am. J. Hematol. 82 (2007) 134
7. Philip A., Kepler J.A., Johnson B.H., and Carroll F.Y. J. Med. Chem. 31 (1988) 870
8. Borissova R., Stjarnkvist P., Karlsson M.O., and Sjoholm I. J. Pharm. Sci. 84 (1995) 256
9. Chung M.C., Gonçalves M.F., Colli W., Ferreira E.I., and Miranda M.T.M. J. Pharm. Sci. 86 (1997) 1127
10. Portela M.J., Moreira R., Valente E., Constantino L., Iley J., Pinto J., Rosa R., Cravo P., and Rosário V.E. Pharm. Res. 16 (1999) 949
11. Rasmussen G.J., and Bundgaard H. Int. J. Pharm. 71 (1991) 45
12. Bak A., Fich M., Larsen B.D., Frokjaer S., and Friis G.J. Eur. J. Pharm. Sci. 7 (1999) 317
13. Gomes P., Araújo M.J., Rodrigues M., Vale N., Azevedo Z., Iley J., Chambel P., Morais J., and Moreira R. Tetrahedron 60 (2004) 5551
14. Araújo M.J., Bom J., Capela R., Casimiro C., Chambel P., Gomes P., Iley J., Lopes F., Morais J., Moreira R., Oliveira E., Rosário V., and Vale N. J. Med. Chem. 48 (2005) 888
15. Vale N., Collins M.S., Gut J., Ferraz R., Rosenthal P.J., Cushion M.T., Moreira R., and Gomes P. Bioorg. Med. Chem. Lett. 18 (2008) 485
16. Chambel P., Capela R., Lopes F., Iley J., Morais J., Gouveia L., Gomes J.R.B., Gomes P., and Moreira R. Tetrahedron 62 (2006) 9883
17. Nodiff E.A., Chatterjee S., and Musallam H.A. Prog. Med. Chem. 28 (1991) 1
18. Ferraz R., Gomes J.R.B., Oliveira E., Moreira R., and Gomes P. J. Org. Chem. 72 (2007) 4189
19. Rinnová M., Nefzi A., and Houghten R.A. Tetrahedron Lett. 43 (2002) 2343
20. +) = 514.21 (calcd, 514.30). The different coupling methods assayed for the preparation of compounds 6 and the corresponding yields are in the Supporting Information, together with spectroscopic data.
21. 4 and evaporated to dryness. Chromatographically homogeneous yellow-orange oils were obtained and identified as the target structures 5 (cf. Supporting Information).
22. See Supporting Information for detailed spectroscopic data.
23. Brossi A., Millet P., Landau I., Bembenek M.E., and Abell C.W. FEBS Lett. 214 (1987) 291
24. Coleman R.E., Vaughan J.A., Hayes D.O., Hollingdale M.R., and Do Rosário V.E. Acta Leiden. 57 (1988) 61
25. Coleman R.E., Clavin A.M., and Milhous W.K. Am. J. Trop. Med. Hyg. 46 (1992) 169
26. Coleman R.E., Nath A.K., Schneider I., Song G.-H., Klein T.A., and Milhous W.K. Am. J. Trop. Med. Hyg. 50 (1994) 646
27. Vangapandu S., Sachdeva S., Jain R., Jain M., Singh S., Singh P.P., Kaul C.L., and Jain R. Bioorg. Med. Chem. 12 (2004) 239