Metallocene-based antimalarials: An exploration into the influence of the ferrocenyl moiety on in vitro antimalarial activity in chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 20, 2007, Pages 6510-6516

  Blackie, Margaret A L ^a   Beagley, Paul ^a   Croft, Simon L ^b   Kendrick, Howard ^b   Moss, John R ^a   Chibale, Kelly ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

^b LONDON SCHOOL OF HYGIENE AND TROPICAL MEDICINE   (United Kingdom)

Author keywords

4 Aminoquinolines; Antimalarial activity; Bioorganometallic; Ferroquine; Metallocene

Indexed keywords

CHLOROQUINE; FERROCENE DERIVATIVE; QUINOLINE DERIVATIVE; RUTHENIUM;

ANTIMALARIAL ACTIVITY; ARTICLE; COMPARATIVE STUDY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HYDROPHOBICITY; IN VITRO STUDY; NONHUMAN; PLASMODIUM FALCIPARUM;

ANIMALS; ANTIMALARIALS; CHLOROQUINE; DRUG RESISTANCE; FERROUS COMPOUNDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PLASMODIUM FALCIPARUM; SENSITIVITY AND SPECIFICITY; STRUCTURE-ACTIVITY RELATIONSHIP;

PLASMODIUM FALCIPARUM;

EID: 34548120539     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.07.012     Document Type: Article

References (42)

1. Winstanley P.A. Parasitol. Today 16 (2000) 146-153
2. Weekly Epidemiological Record, W.H.O. 72 (No: I, II, III), 1997; pp. 1-16.
3. Biot C., and Chibale K. Infect. Disorders-Drug Targets 6 (2006) 173-204
4. Wasi N., Singh H.B., Gajanana A., and Raichowdhary A.N. Inorg. Chim. Acta 135 (1987) 133-137
5. Wasi N., and Singh H.B. Synth. React. Inorg. Met.-Org. Chem. 17 (1987) 129-141
6. Wasi N., and Singh H.B. Synth. React. Inorg. Met.- Org. Chem. 18 (1988) 473-485
7. Sánchez-Delgado R.A., Navarro M., Perez H., and Urbina J.A. J. Med. Chem. 39 (1996) 1095-1099
8. Stocks P.A., Raynes K.J., Bray P.G., Park B.K., O'Neill P.M., and Ward S.A. J. Med. Chem. 45 (2002) 4975-4983
9. Blackie M.A.L., Beagley P., Chibale K., Clarkson C., Hutton A.T., Moss J.R., and Smith P.J. J. Organomet. Chem. 689 (2003) 144-152
10. Biot C., Glorian G., Maciejewski L.A., Brocard J.S., Domarle O., Blampain G., Millet P., and George A.J. J. Med. Chem. 40 (1997) 3715-3718
11. Domarle O., Blampain G., Agnaniet H., Nzadiyabi T., Lebibi J., Brocard J., Maciejewski L., Biot C., Georges A.J., and Millet P. Antimicro. Agents Chemother. 42 (1998) 540-544
12. Biot C. Curr. Med. Chem.-Anti-infect. Agents 3 (2004) 135-147
13. Biot C., Daher W., Ndiaye C., 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
14. Chibale K., Moss J.R., Blackie M., van Schalkwyk D., and Smith P.J. Tetrahedron Lett. 41 (2000) 6231-6235
15. Biot, C.; Taramelli, D.; Forfar-Bares, I.; Maciejewski, L. A.; Boyce, M.; Nowogrocki, G.; Brocard, J.; Basilico, N.; Olliaro, P.; Egan T.J. Mol. Pharm. 2, 3, 185-193.
16. Sullivan D.J., Gluzman I.Y., Russell D.G., and Goldberg D.E. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 11865-11870
17. Egan T. Exp. Opin. Ther. Patents 11 (2001) 185-209
18. Kaschula C.H., Egan T.J., Hunter R., Basilico N., Parapini S., Taramelli D., Pasini E., and Monti D. J. Med. Chem. 45 (2002) 3531-3539
19. Egan T.J., Hunter R., Kaschula C.H., Marques H.M., Misplon A., and Walden J. J. Med. Chem. 43 (2000) 283-291
20. Ridley R.G., Hofheinz W., Matile H., Jaquet C., Dorn A., Masciardi R., Jolidon S., Richter W.F., Guenzi A., Girometta M.-A., Urwyler H., Huber W., Thaithong S., and Peters W. Antimicrob. Agents Chemother. 40 (1996) 1846-1854
21. Vennerstrom J.L., Ellis W.Y., Ager Jr. A.L., Andersen S.L., Gerena L., and Milhous W.K. J. Med. Chem. 35 (1992) 2129-2134
22. Vennerstrom J.L., Ager Jr. A.L., Dorn A., Andersen S.L., Gerena L., Ridley R.G., and Milhous W.K. J. Med. Chem. 41 (1998) 4360-4364
23. De D., Krogstad F.M., Byers L.D., and Krogstad D.J. J. Med. Chem. 41 (1998) 4918-4926
24. De D., Krogstad F.M., Cogswell F.B., and Krogstad D.J. Am. J. Trop. Med. Hyg. 55 (1996) 579-583
25. O'Neill P.M., Willock D.J., Hawley S.R., Bray P.G., Storr R.C., Ward S.A., and Park B.K. J. Med. Chem. 40 (1997) 437-448
26. Beagley P., Blackie M.A.L., Chibale K., Clarkson C., Moss J.R., and Smith P.J. J. Chem. Soc. Dalton Trans. (2002) 4426-4433
27. Beagley P., Blackie M.A.L., Chibale K., Clarkson C., Meijboom R., Moss J.R., Smith P.J., and Su H. Dalton Trans. (2003) 3046-3051
28. Picart-Goetgheluck S., Delacroix O., Maciejewski L., and Brocard J. Synthesis 10 (2000) 1421-1426
29. Pigeon P., Top S., Vessières A., Huché M., Hillard E.A., Salomon E., and Jaouen G. J. Med. Chem. 48 (2005) 2814-2821
30. De D., Byers L.D., and Krogstad D.J. J. Heterocycl. Chem. 34 (1997) 315-320
31. Blackie, M. A. L., Ph.D. Thesis.
32. Henry D.W. Chem. Heterocycl. Compd. 9 (1973) 829-850
33. Chen T.K., Fico R., and Canellakis E.S. J. Med. Chem. 21 (1978) 868-874
34. Gamage S.A., Tepsiri N., Wilairat P., Wojcik S.J., Figgitt D., Ralph R.K., and Denny W.A. J. Med. Chem. 37 (1994) 1486-1494
35. Dorn A., Vippagunta S.R., Matile H., Jaquet C., Vennerstrom J.L., and Ridley R.G. Biochem. Pharmacol. 55 (1998) 727-736
36. Hawley S.R., Bray P.G., O'Neill P.M., Park B., and Ward S.A. Biochem. Pharmacol. 52 (1996) 723-733
37. Hawley S.R., Bray P.G., Mungthin M., Atkinson J.D., O'Neill P.M., and Ward SA. Antimicro. Agents Chemother. 42 (1998) 682-686
38. O'Neill P.M., Willock D.J., Hawley S.R., Bray P.G., Storr R.C., Ward S.A., and Park B.K. J. Med. Chem. 40 (1997) 437-448
39. Silverman G.S. In: Silverman G.S., and Rakita P.E. (Eds). Handbook of Grignard Reagents (1996), Marcel Dekker Inc., New York 89-92 Chapter 6
40. Makler M.T., and Hinrichs D.J. Am. J. Trop. Med. Hyg. 48 (1993) 205-210
41. Desjardins R.E., Canfield C.J., Haynes J.D., and Chulay J.D. Antimicrob. Agents Chemother. 16 (1979) 710-718
42. O'Neill M.J., Bray D.H., Boardman P., Phillipson J.D., and Warhurst D.C. Planta Med. 5 (1985) 394-398