New ferrocenic pyrrolo[1,2-a]quinoxaline derivatives: Synthesis, and in vitro antimalarial activity

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 20, 2008, Pages 9133-9144

  Guillon, Jean ^a   Moreau, Stéphane ^a   Mouray, Elisabeth ^b   Sinou, Véronique ^c   Forfar, Isabelle ^a   Fabre, Solene Belisle ^a   Desplat, Vanessa ^d   Millet, Pascal ^d   Parzy, Daniel ^c   Jarry, Christian ^a   Grellier, Philippe ^b  

^a Laboratoire de Pharmacochimie   (France)

^b MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

^c SERVICE DE SANTÉ DES ARMÉES   (France)

^d UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

Antimalarial activity; Ferrocenic pyrrolo 1,2 a quinoxaline derivatives; Synthesis

Indexed keywords

ARTEMISININ; BIS[N (PYRROLO[1,2 A]QUINOXALIN 4 YL) 3 AMINOPROPYL] N FERROCENYLMETHYLAMINE; CHLOROQUINE; FERROCENE DERIVATIVE; HEMOZOIN; PYRROLO[1,2 A]QUINOXALINE DERIVATIVE; QUINOXALINE DERIVATIVE; SULFADIMETHOXINE; UNCLASSIFIED DRUG;

AMINATION; ANTIMALARIAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; NONHUMAN; PLASMODIUM FALCIPARUM; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

PLASMODIUM FALCIPARUM;

EID: 53449089591     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.09.038     Document Type: Article

References (51)

1. Mishra S.K., Satpathy S.K., and Mohanty S. Bull. World Health Organ. 77 (1999) 1020
2. B Bouland P. Drug Resistance in Malaria (2001), World Health Organization, Switzerland
3. Ridley R.G. Nature 415 (2002) 686-693
4. Hastings I.M. Trends Parasitol. 20 (2004) 512-518
5. Gelb M.H., and Hol W.G.J. Science 297 (2002) 343-344
6. Surrey A.R., and Hammer H.F. J. Am. Chem. Soc 68 (1946) 113-116
7. White N.J. J. Antimicrob. Chemother. 30 (1992) 571-585
8. Van Est H.G., Skamene G.E., and Schurr E. Clin. Invest. Med. 16 (1993) 285-293
9. Vennerstrom J.L., Ager A.L., Dorn A., Andersen S.L., Gerena L., Ridley R.G., and Milhous W.K. J. Med. Chem. 41 (1998) 4360-4364
10. Raynes K. Int. J. Parasitol. 29 (1999) 367-379
11. Girault S., Grellier P., Berecibar A., Maes L., Mouray E., Lemière P., Debreu M.A., Davioud-Charvet E., and Sergheraert C. J. Med. Chem 43 (2000) 2646-2654
12. Girault S., Delarue S., Grellier P., Berecibar A., Maes L., Quirijnen L., Lemière P., Debreu-Fontaine M.A., and Sergheraert C. J. Pharm. Pharmacol. 53 (2001) 935-938
13. Ryckebusch A., Déprez-Poulain R., Debreu-Fontaine M.-A., Vandaele R., Mouray E., Grellier P., and Sergheraert C. Bioorg. Med. Chem. Lett. 12 (2002) 2595-2598
14. Ryckebusch A., Déprez-Poulain R., Debreu-Fontaine M.-A., Vandaele R., Mouray E., Grellier P., and Sergheraert C. Bioorg. Med. Chem. Lett. 13 (2003) 3783-3787
15. Ryckebusch A., Déprez-Poulain R., Maes L., Debreu-Fontaine M.-A., Mouray E., Grellier P., and Sergheraert C. J. Med. Chem. 46 (2003) 542-557
16. Ryckebusch A., Debreu-Fontaine M.-A., Mouray E., Grellier P., Sergheraert C., and Melnyk P. Bioorg. Med. Chem. Lett. 15 (2005) 297-302
17. Dombrowski K.E., Baldwin W., and Sheats J.E. J. Organomet. Chem. 302 (1986) 281-306
18. Jaouen G., Vessieres A., and Butler I. Acc. Chem. Res. 26 (1993) 361-369
19. Pradines B., Orlandi-Pradines E., Henry M., Bogreau H., Fusai T., Mosnier J., Baret E., Durand C., Bouchiba H., Penhoat K., and Rogier C. Ann. Pharm. Fr. 63 (2005) 284-294
20. Biot C., Glorian G., Maciejewski L.A., Brocard J.S., Domarle O., Blampain G., Millet P., Georges A.J., Abessolo H., Dive D., and Lebibi J. J. Med. Chem. 40 (1997) 3715-3718
21. Dive D., and Biot C. ChemMedChem 3 (2008) 383-391
22. Domarle O., Blampain G., Agnaniet H., Nzadiyabi T., Lebibi J., Brocard J.S., Maciejewski L.A., Biot C., Georges A.J., and Millet P. Antimicrob. Chemother. 42 (1998) 540-544
23. Attake C., Mezui Me Ndong J., Aubouy A., Maciejewski L.A., Brocard J., Lébibi J., and Deloron P. J. Antimicrob. Chemother. 51 (2003) 1021-1024
24. Biot C., Delhaes L., N'Diaye C.M., Maciejewski L.A., Camus D., Dive D., and Brocard J.S. Bioorg. Med. Chem. 7 (1999) 2843-2847
25. Biot C., Daher W., N'Diaye C.M., Melnyk P., Pradines B., Chavain N., Pellet A., Fraisse L., Pelinski L., Jarry C., Brocard J., Khalife J., Forfar-Bares I., and Dive D. J. Med. Chem. 49 (2006) 4707-4714
26. Biot C., Dessolin J., Ricard I., and Dive D. J. Organomet. Chem. 689 (2004) 4678-4682
27. Biot C., Delhaes L., Maciejewski L.A., Mortuaire M., Camus D., Dive D., and Brocard J.S. Eur. J. Med. Chem. 35 (2000) 707-714
28. Guillon J., Forfar I., Mamani-Matsuda M., Desplat V., Saliège M., Thiolat D., Massip S., Tabourier A., Léger J.-M., Dufaure B., Haumont G., Jarry C., and Mossalayi D. Bioorg. Med. Chem. 15 (2007) 194-210
29. Guillon J., Forfar I., Desplat V., Belisle Fabre S., Thiolat D., Massip S., Carrie H., Mossalayi D., and Jarry C. J. Enzyme Inhib. Med. Chem. 22 (2007) 541-549
30. Guillon J., Boulouard M., Lisowski V., Stiebing S., Lelong V., Dallemagne P., and Rault S. J. Pharm. Pharmacol. 52 (2000) 1369-1375
31. Guillon J., Grellier P., Labaied M., Sonnet P., Léger J.-M., Déprez-Poulain R., Forfar-Bares I., Dallemagne P., Lemaître N., Péhourcq F., Rochette J., Sergheraert C., and Jarry C. J. Med. Chem. 47 (2004) 1997-2009
32. Guari Y., van Es D.S., Reek J.N.H., Kamer P.C.J., and van Leeuwen P.W.N.M. Tetrahedron Lett. 40 (1999) 3789-3790
33. Garnier E., Audoux J., Pasquinet E., Suzenet F., Poullain D., Lebret B., and Guillaumet G. J. Org. Chem. 69 (2004) 7809-7815
34. Abad A., Agullo C., Cunat A.C., and Vilanova C. Synthesis 6 (2005) 915-924
35. Carlier P.R., Chow E.S.H., Han Y., Liu J., El Yazal J., and Pang Y.-P. J. Med. Chem. 42 (1999) 4225-4231
36. Hess A., Sehnert J., Weyhermüller T., and Metzler-Nolte N. Inorg. Chem. 39 (2000) 5437-5443
37. Chen W.-Y., Lu J., Shen Z.-X., and Zhang Y.-W. Chin. J. Chem. 22 (2004) 306-309
38. Vennerstrom J.L., Ellis W.Y., Ager A.L., Andersen S.L., Gerena L., and Milhous W.K. J. Med. Chem. 35 (1992) 2129-2134
39. Raynes K., Galatis D., Cowman A.F., Tilley L., and Deady L.W. J. Med. Chem. 38 (1995) 204-206
40. Egan T.J., and Marques H.M. Coord. Chem. Rev. 190-192 (1999) 493-517
41. Hawley S.R., Bray P.G., Mungthin M., Atkinson J.D., O'Neill P.M., and Ward S.A. Antimicrob. Agents Chemother. 42 (1998) 682-686
42. Buller R., Peterson M.L., Almarsson O., and Leiserowitz L. Cryst. Growth Des. 2 (2002) 553-562
43. Sullivan D.J. Int. J. Parasitol. 32 (2002) 1645-1653
44. Slater A.F.G., and Cerami A. Nature 355 (1992) 167-169
45. Sullivan D.J., Matile H., Ridley R.G., and Goldberg D.E. J. Biol. Chem. 273 (1998) 31103-31107
46. Basilico N., Pagani E., Monti D., Olliaro P., and Taramelli D. J. Antimicrob. Chemother. 42 (1998) 55-60
47. Nzila A. J. Antimicrob. Chemother. 57 (2006) 1043-1054
48. Meshnick S.R. Int. J. Parasitol. 32 (2002) 1655-1660
49. Bhal S.K., Kassam K., Peirson G.I., and Pearl G.M. Mol. Pharm. 4 (2007) 556-560
50. Trager W., and Jensen J.B. Science 193 (1976) 673-677
51. Desjardins R.E., Canfield C.J., Haynes J.D., and Chulay J.D. Antimicrob. Agents Chemother. 16 (1979) 710-718