Synthesis and Biological Evaluation of Acridine Derivatives as Antimalarial Agents

ChemMedChem

Volumn 7, Issue 4, 2012, Pages 587-605

  Yu, Xiao Min ^a,b   Ramiandrasoa, Florence ^a,b   Guetzoyan, Lucie ^a,b   Pradines, Bruno ^b   Quintino, Edgar ^a,b   Gadelle, Daniele ^a,b   Forterre, Patrick ^a,b   Cresteil, Thierry ^b   Mahy, Jean Pierre ^a,b   Pethe, Stéphanie ^a,b  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNRS   (France)

Author keywords

hematin; Aminoacridines; Antiparasitic agents; Malaria; Plasmodium falciparum; Topoisomerases

Indexed keywords

2 (2 BROMOETHYL) 1H ISOINDOLE 1,3(2H) DIONE; 2 (2 MORPHOLIN 4 YLETHYL) 1H ISOINDOLE 1,3(2H) DIONE; 2 (4 BROMOBUTYL) 1H ISOINDOLE 1,3(2H) DIONE; 2 (4 MORPHOLIN 4 YLBUTYL) 1H ISOINDOLE 1,3(2H) DIONE; 2 (6 BROMOHEXYL) 1H ISOINDOLE 1,3(2H) DIONE; 2 (6 MORPHOLIN 4 YLHEXYL) 1H ISOINDOLE 1,3(2H) DIONE; 2 MORPHOLIN 4 YLETHANAMINE; 4 MORPHOLIN 4 YLBUTANAMINE; 6 CHLORO 2 METHOXY N (2 MORPHOLIN 4 YLETHYL) 9 ACRIDINAMINE; 6 CHLORO 2 METHOXY N (2 PIPERAZIN 1 YLETHYL) 9 ACRIDINAMINE; 6 CHLORO 2 METHOXY N (4 MORPHOLIN 4 YLBUTYL) 9 ACRIDINAMINE; 6 CHLORO 2 METHOXY N (4 PIPERAZIN 1 YLBUTYL) 9 ACRIDINAMINE; 6 CHLORO 2 METHOXY N (6 MORPHOLIN 4 YLHEXYL) 9 ACRIDINAMINE; 6 CHLORO 2 METHOXY N (6 PIPERAZIN 1 YLHEXYL) 9 ACRIDINAMINE; 6 MORPHOLIN 4 YLHEXANAMINE; ACRIDINE DERIVATIVE; ANTIMALARIAL AGENT; N (2 PIPERAZIN 1 YLETHYL) 9 ACRIDINAMINE; N (4 PIPERAZIN 1 YLBUTYL) 9 ACRIDINAMINE; N (6 PIPERAZIN 1 YLHEXYL) 9 ACRIDINAMINE; N (ACRIDIN 9 YL) 1,4 BUTANEDIAMINE; N (ACRIDIN 9 YL) 1,6 HEXANEDIAMINE; N [2 (6 CHLORO 2 METHOXYACRIDIN 9 YLAMINO)ETHYL] 2 AMINO 3 (1H IMIDAZOL 4 YL)PROPIONAMIDE; N [2 (6 CHLORO 2 METHOXYACRIDIN 9 YLAMINO)ETHYL]PYRROLYDIN 2 YLCARBOXAMIDE; N [2 (ACRIDIN 9 YLAMINO)ETHYL] 2 AMINO 3 (1H IMIDAZOL 4 YL)PROPIONAMIDE; N [4 (6 CHLORO 2 METHOXYACRIDIN 9 YLAMINO)BUTYL] 2 AMINO 3 (1H IMIDAZOL 4 YL)PROPIONAMIDE; N [4 (6 CHLORO 2 METHOXYACRIDIN 9 YLAMINO)BUTYL]PYRROLYDIN 2 YLCARBOXAMIDE; N [6 (6 CHLORO 2 METHOXYACRIDIN 9 YLAMINO)HEXYL] 2 AMINO 3 (1H IMIDAZOL 4 YL)PROPIONAMIDE; N [6 (ACRIDIN 9 YLAMINO)HEXYL] 2 AMINO 3 (1H IMIDAZOL 4 YL)PROPIONAMIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTALLIZATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; NONHUMAN; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; SULFOLOBUS SHIBATAE;

ACRIDINES; AMINACRINE; ANTIMALARIALS; CELL LINE; CHLOROQUINE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; DRUG RESISTANCE, MICROBIAL; HEME; HEMEPROTEINS; HUMANS; HYDROGEN-ION CONCENTRATION; INHIBITORY CONCENTRATION 50; KB CELLS; MOLECULAR STRUCTURE; PLASMODIUM FALCIPARUM; SULFOLOBUS; TOPOISOMERASE INHIBITORS;

EID: 84859196773     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201100554     Document Type: Article

References (63)

1. World Malaria Report 2008, World Health Organization, (accessed January 26, 2012).
2. N. J. White, Science 2008, 320, 330-334.
3. A. M. Dondorp, S. Yeung, L. White, C. Nguon, N. P. J. Day, D. Socheat, L. vonSeidlein, Nat. Rev. Microbiol. 2010, 8, 272-280.
4. B. Pradines, J. Dormoi, S. Briolant, H. Bogreau, C. Rogier, Rev. Francoph. Lab. 2010, 2010, 51-62.
5. C. C. Musonda, S. Little, V. Yardley, K. Chibale, Bioorg. Med. Chem. Lett. 2007, 17, 4733-4736.
6. T.-S. Feng, E. M. Guantai, M. Nell, C. E. J. vanRensburg, K. Ncokazi, T. J. Egan, H. C. Hoppe, K. Chibale, Biochem. Pharmacol. 2011, 82, 236-247.
7. S. Vispé, I. Vandenberghe, M. Robin, J. P. Annereau, L. Créancier, V. Pique, J. P. Galy, A. Kruczynski, J. M. Barret, C. Bailly, Biochem. Pharmacol. 2007, 73, 1863-1872.
8. M. Jones, A. E. Mercer, P. A. Stocks, L. J. I. LaPensée, R. Cosstick, B. K. Park, M. E. Kennedy, I. Piantanida, S. A. Ward, J. Davies, P. G. Bray, S. L. Rawe, J. Baird, T. Charidza, O. Janneh, P. M. O'Neill, Bioorg. Med. Chem. Lett. 2009, 19, 2033-2037.
9. A. Kumar, K. Srivastava, S. RajaKumar, S. K. Puri, P. M. S. Chauhan, Bioorg. Med. Chem. Lett. 2010, 20, 7059-7063.
10. M. O. Anderson, J. Sherrill, P. B. Madrid, A. P. Liou, J. L. Weisman, J. L. DeRisi, R. K. Guy, Bioorg. Med. Chem. 2006, 14, 334-343.
11. J. Y. Hwang, T. Kawasuji, D. J. Lowes, J. A. Clark, M. C. Connelly, F. Zhu, W. A. Guiguemde, M. S. Sigal, E. B. Wilson, J. L. DeRisi, R. K. Guy, J. Med. Chem. 2011, 54, 7084-7093.
12. S. Kumar, M. Guha, V. Choubey, P. Maity, U. Bandyopadhyay, Life Sci. 2007, 80, 813-828.
13. M. Henry, S. Alibert, E. Orlandi-Pradines, H. Bogreau, T. Fusai, C. Rogier, J. Barbe, B. Pradines, Curr. Drug Targets 2006, 7, 935-948.
14. M. Henry, S. Alibert, C. Rogier, J. Barbe, B. Pradines, Curr. Top. Med. Chem. 2008, 8, 563-578.
15. P. Olliaro, Pharmacol. Ther. 2001, 89, 207-219.
16. P. D. Roepe, Future Microbiol. 2009, 4, 441-455.
17. J. M. Wright, L. A. Dunn, P. Upcroft, J. A. Upcroft, Expert Opin. Drug Saf. 2003, 2, 529-541.
18. S. Kalia, J. P. Dutz, Dermatol. Ther. 2007, 20, 160-174.
19. O. Dikensoy, R. W. Light, Curr. Opin. Pulm. Med. 2005, 11, 340-344.
20. J. Zipper, E. Kessel, Int. J. Gynecol. Obstet. 1998, 83, S7-S11.
21. A. K. Tshefu, O. Gaye, K. Kayentao, R. Thompson, K. M. Bhatt, S. S. Sesay, D. G. Bustos, E. Tjitra, G. Bedu-Addo, I. Borghini-Fuhrer, S. Duparc, C. S. Shin, L. Fleckenstein, Lancet 2010, 375, 1457-1467.
22. C. Chen, L.-H. Tang, J. Chun, Trans. R. Soc. Trop. Med. Hyg. 1992, 86, 7-10.
23. S. Looareesuwan, D. E. Kyle, C. Viravan, S. Vanijanonta, P. Wilairatana, W. Wernsdorfer, Am. J. Trop. Med. Hyg. 1996, 54, 205-209.
24. S. Looareesuwan, P. Olliaro, D. Kyle, W. Wernsdorfer, S. Foster, Lancet 1996, 347, 1189-1190.
25. P. Ringwald, E. C. M. Eboumbou, J. Bickii, L. K. Basco, Antimicrob. Agents Chemother. 1999, 43, 1525-1527.
26. P. Ringwald, J. Bickii, L. K. Basco, Clin. Infect. Dis. 1998, 26, 946-953.
27. B. Pradines, M. Mabika Mamfoumbi, D. Parzy, M. Owono Medang, C. Lebeau, J. R. Mourou Mbina, J. C. Doury, M. Kombila, Am. J. Trop. Med. Hyg. 1999, 60, 105-108.
28. B. Pradines, A. Tall, D. Parzy, A. Spiegel, T. Fusai, R. Hienne, J. F. Trape, J. C. Doury, J. Antimicrob. Chemother. 1998, 42, 333-339.
29. B. Pradines, S. Briolant, M. Henry, C. Oeuvray, E. Baret, R. Amalvict, E. Didillon, C. Rogier, Malar. J. 2010, 9, 339.
30. H. Yang, D. Liu, Y. Yang, K. Huang, Y. Dong, P. Yang, M. Liao, C. Zhang, Southeast Asian J. Trop. Med. Public Health 1997, 28, 460-464.
31. L. R. Ferguson, W. A. Denny, Mutat. Res. 2007, 623, 14-23.
32. P. Chavalitshewinkoon, P. Wilairat, S. Gamage, W. Denny, D. Figgitt, R. Ralph, Antimicrob. Agents Chemother. 1993, 37, 403-406.
33. C. Santelli-Rouvier, B. Pradines, M. Berthelot, D. Parzy, J. Barbe, Eur. J. Med. Chem. 2004, 39, 735-744.
34. M. K. Azim, W. Ahmed, I. A. Khan, N. A. Rao, K. M. Khan, Bioorg. Med. Chem. Lett. 2008, 18, 3011-3015.
35. L. Guetzoyan, F. Ramiandrasoa, H. Dorizon, C. Desprez, A. Bridoux, C. Rogier, B. Pradines, M. Perree-Fauvet, Bioorg. Med. Chem. 2007, 15, 3278-3289.
36. L. Guetzoyan, X.-M. Yu, F. Ramiandrasoa, S. Pethe, C. Rogier, B. Pradines, T. Cresteil, M. Perree-Fauvet, J.-P. Mahy, Bioorg. Med. Chem. 2009, 17, 8032-8039.
37. M. Casagrande, N. Basilico, C. Rusconi, D. Taramelli, A. Sparatore, Bioorg. Med. Chem. 2010, 18, 6625-6633.
38. D. Warhurst, J. Craig, I. Adagu, D. Meyer, S. Lee, Malar. J. 2003, 2, 26.
39. F. Lombardo, R. S. Obach, M. Y. Shalaeva, F. Gao, J. Med. Chem. 2004, 47, 1242-1250.
40. J. Kornhuber, P. Tripal, M. Reichel, L. Terfloth, S. Bleich, J. Wiltfang, E. Gulbins, J. Med. Chem. 2008, 51, 219-237.
41. S. Parapini, N. Basilico, E. Pasini, T. J. Egan, P. Olliaro, D. Taramelli, D. Monti, Exp. Parasitol. 2000, 96, 249-256.
42. S. Gemma, G. Kukreja, C. Fattorusso, M. Persico, M. P. Romano, M. Altarelli, L. Savini, G. Campiani, E. Fattorusso, N. Basilico, D. Taramelli, V. Yardley, S. Butini, Bioorg. Med. Chem. Lett. 2006, 16, 5384-5388.
43. S. Auparakkitanon, W. Noonpakdee, R. K. Ralph, W. A. Denny, P. Wilairat, Antimicrob. Agents Chemother. 2003, 47, 3708-3712.
44. F. Omodeo-Sale, L. Cortelezzi, N. Basilico, M. Casagrande, A. Sparatore, D. Taramelli, Antimicrob. Agents Chemother. 2009, 53, 4339-4344.
45. J. R. Goodell, A. A. Madhok, H. Hiasa, D. M. Ferguson, Bioorg. Med. Chem. 2006, 14, 5467-5480.
46. L. M. Oppegard, A. V. Ougolkov, D. N. Luchini, R. A. Schoon, J. R. Goodell, H. Kaur, D. D. Billadeau, D. M. Ferguson, H. Hiasa, Eur. J. Pharmacol. 2009, 602, 223-229.
47. D. K. Trask, J. A. DiDonato, M. T. Muller, EMBO J. 1984, 3, 671-676.
48. A. Bergerat, B. deMassy, D. Gadelle, P.-C. Varoutas, A. Nicolas, P. Forterre, Nature 1997, 386, 414-417;
49. PlasmoDB: Plasmodium Genomics Resource, (accessed January 27, 2012).
50. Y. Pommier, E. Leo, H. Zhang, C. Marchand, Chem. Biol. 2010, 17, 421-433.
51. I. Opsenica, J. Burnett, R. Gussio, D. Opsenica, N. Todorovic, C. Lanteri, R. Sciotti, M. Gettayacamin, N. Basilico, D. Taramelli, J. E. Nuss, L. Wanner, R. G. Panchal, B. A. Solaja, S. Bavari, J. Med. Chem. 2011, 54, 1157-1169.
52. K. Ohara, M. Smietana, A. Restouin, S. Mollard, J.-P. Borg, Y. Collette, J.-J. Vasseur, J. Med. Chem. 2007, 50, 6465-6475.
53. J. C. Sheehan, W. A. Bolhofer, J. Am. Chem. Soc. 1950, 72, 2786-2788.
54. S. Sengmany, E. LeGall, C. LeJean, M. Troupel, J.-Y. Nédélec, Tetrahedron 2007, 63, 3672-3681.
55. A. R. Brown, D. C. Rees, Z. Rankovic, J. R. Morphy, J. Am. Chem. Soc. 1997, 119, 3288-3295.
56. A. Postma, T. P. Davis, R. A. Evans, G. Li, G. Moad, M. S. O'Shea, Macromolecules 2006, 39, 5293-5306.
57. A. Kossanyi, B. Mestre, M. Perrée-Fauvet, Synth. Commun. 1999, 29, 4341.
58. C. Buhler, D. Gadelle, P. Forterre, J. C. Wang, A. Bergerat, Nucleic Acids Res. 1998, 26, 5157-5162.
59. M. Henry, S. Briolant, A. Fontaine, J. Mosnier, E. Baret, R. Amalvict, T. Fusai, L. Fraisse, C. Rogier, B. Pradines, Antimicrob. Agents Chemother. 2008, 52, 2755-2759.
60. M. Henry, S. Briolant, A. Zettor, S. Pelleau, M. Baragatti, E. Baret, J. Mosnier, R. Amalvict, T. Fusai, C. Rogier, B. Pradines, Antimicrob. Agents Chemother. 2009, 53, 1926-1930.
61. V. Parquet, S. Briolant, M. Torrentino-Madamet, M. Henry, L. Almeras, R. Amalvict, E. Baret, T. Fusai, C. Rogier, B. Pradines, Antimicrob. Agents Chemother. 2009, 53, 2248-2252.
62. H. Bogreau, F. Renaud, H. Bouchiba, P. Durand, S.-B. Assi, M.-C. Henry, E. Garnotel, B. Pradines, T. Fusai, B. Wade, E. Adehossi, P. Parola, M. A. Kamil, O. Puijalon, C. Rogier, Am. J. Trop. Med. Hyg. 2006, 74, 953-959.
63. M. Henry, I. Diallo, J. Bordes, S. Ka, B. Pradines, B. Diatta, P. S. M′Baye, M. Sane, M. Thiam, P. M. Gueye, B. Wade, J.-E. Touze, J.-M. Debonne, C. Rogier, T. Fusai, Am. J. Trop. Med. Hyg. 2006, 75, 146-151.