Synthesis and antimalarial evaluation of new N 1-(7-chloro-4- quinolyl)-1,4-bis(3-aminopropyl)piperazine derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 2, 2005, Pages 297-302

  Ryckebusch, Adina ^a   Debreu Fontaine, Marie Ange ^a   Mouray, Elisabeth ^b   Grellier, Philippe ^b   Sergheraert, Christian ^a   Melnyk, Patricia ^a  

^a INSTITUT PASTEUR DE LILLE   (France)

^b USM 0504   (France)

Author keywords

Antimalarial activity; Piperazine derivatives; Quinoline

Indexed keywords

ANTIMALARIAL AGENT; CHLOROQUINE; PIPERAZINE DERIVATIVE;

ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG MECHANISM; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; DRUG TARGETING; HYPOTHESIS; NONHUMAN; PLASMODIUM FALCIPARUM;

ANIMALS; ANTIMALARIALS; CELL LINE; CHLOROQUINE; CHROMATOGRAPHY, AFFINITY; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; PARASITIC SENSITIVITY TESTS; PIPERAZINES; PLASMODIUM FALCIPARUM;

PLASMODIUM FALCIPARUM;

EID: 10644221022     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.10.080     Document Type: Article

References (22)

1. R.G. Ridley Nature 415 2002 686 693
2. P.A. Stocks, K.J. Raynes, P.G. Bray, B.K. Park, P.M. O'Neill, and S.A. Ward J. Med. Chem. 45 2002 4975 4983
3. P.M. O'Neill, A. Mukhtar, P.A. Stocks, L.E. Randle, S. Hindley, S.A. Ward, R.C. Storr, J.F. Bickley, I.A. O'Neil, J.L. Maggs, R.H. Hughes, P.A. Winstanley, P.G. Bray, and B.K. Park J. Med. Chem. 46 2003 4933 4945
4. D. De, F.M. Krogstad, F.B. Cogswell, and D.L. Krogstad Am. J. Trop. Med. Hyg. 55 1995 579 583
5. D. De, F.M. Krogstad, L.D. Byers, and D.L. Krogstad J. Med. Chem. 41 1998 4926 4941
6. R.G. Ridley, W. Hofheinz, H. Matile, C. Jaquet, A. Dorn, R. Masciadri, S. Jolidon, W.F. Richter, A. Guenzi, M.A. Girometta, H. Urwyler, W. Huber, S. Thaithong, and W. Peters Antimicrob. Agents Chemother. 40 1996 1846 1854
7. S.R. Hawley, P.G. Bray, P.M. O'Neill, B.K. Park, and S.A. Ward Mol. Biochem. Parasitol. 80 1996 15 25
8. D.J. Krogstad, I.Y. Gluzman, D.E. Kyle, A.M. Oduola, S.K. Martin, W.K. Milhous, and P.H. Schlesinger Science 238 1987 1283 1285
9. T.J. Egan Exp. Opin. Ther. Pat. 11 2001 185 209
10. A. Ryckebusch, R. Déprez-Poulain, M.-A. Debreu-Fontaine, R. Vandaele, E. Mouray, P. Grellier, and C. Sergheraert Bioorg. Med. Chem. Lett. 12 2002 2595 2598
11. A. Ryckebusch, R. Déprez-Poulain, L. Maes, M.-A. Debreu-Fontaine, E. Mouray, P. Grellier, and C. Sergheraert J. Med. Chem. 46 2003 542 557
12. Two mice out of three died owing to toxicity at 40 mg/kg of compound 1
13. 4, the solvent was evaporated and the residue was purified by thick layer chromatography to yield the desired product
14. 2); MALDI-MS m/z = 416.2
15. R 12.26 min, MALDI-MS m/z = 444.1
16. W. Trager, and J.B. Jensen Science 193 1976 673 677
17. R.E. Desjardins, C.J. Canfield, J.D. Haynes, and J.D. Chulay Antimicrob. Agents Chemother. 16 1979 710 718
18. T. Mossman J. Immunol. Methods 65 1983 55 63
19. A. Ryckebusch, R. Déprez-Poulain, M.-A. Debreu-Fontaine, R. Vandaele, E. Mouray, P. Grellier, and C. Sergheraert Bioorg. Med. Chem. Lett. 13 2003 2787 3783
20. T.J. Egan, R. Hunter, C.H. Kaschula, H.M. Marques, A. Misplon, and J. Walden J. Med. Chem. 43 2000 283 291
21. S.R. Cheruku, S. Maiti, A. Dorn, B. Scorneaux, A.K. Bhattacharjee, W.Y. Ellis, and J.L. Vennerstrom J. Med. Chem. 46 2003 3166 3169
22. S. Hawley, P.C. Bray, P.M. O'Neill, B.K. Park, and S.A. Ward Biochem. Pharmacol. 52 1996 723 733