Synthesis, cytotoxicity and antimalarial activity of ferrocenyl amides of 4-aminoquinolines

Arzneimittel-Forschung/Drug Research

Volumn 60, Issue 10, 2010, Pages 627-635

  N'Da, David D ^a   Breytenbach, Jaco C ^a   Smith, Peter J ^b   Lategan, Carmen ^b  

^a NORTH WEST UNIVERSITY   (South Africa)

^b UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

4 aminoquinolines; Antimalarial activity; Cytotoxicity; Ferrocene; Plasmodium falciparum

Indexed keywords

1 N (7 CHLOROQUINOLINYL YL)BENZENE 1,4 DIAMINE; 2 NITROPHENYL 4 FERROCENYLBUTANOATE; 2 NITROPHENYL FERROCENYLFORMATE; 4 (7 CHLOROQUINOLIN 4 YL)PIPERAZINE 1 CARBONYLFERROCENE; 4 AMINOQUINOLINE; 4 FERROCENYL 1 [4 (7 CHLOROQUINOLIN 4 YL)PIPERAZIN 1 YL]BUTAN 1 ONE; 4 FERROCENYL N [2 [(7 CHLOROQUINOLIN 4 YL)AMINO]BUTYL]BUTANAMIDE; 4 FERROCENYL N [2 [(7 CHLOROQUINOLIN 4 YL)AMINO]ETHYL]BUTANAMIDE; 4 FERROCENYL N [2 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL]BUTANAMIDE; 4 FERROCENYL N [2 [(7 CHLOROQUINOLIN 4 YL)AMINO]PROPYL]BUTANAMIDE; 4 FERROCENYL N [4 [(6 METHOXYQUINOLIN 8 YL)AMINO]PENTYL]BUTANAMIDE; 4 FERROCENYLBUTANOIC ACID; 4,7 DICHLOROQUINOLINE; 7 CHLORO 4 (PIPERAZIN 1 YL)QUINOLINE; CHLOROQUINE; FERROCENE DERIVATIVE; FERROCENYLFORMIC ACID; MEFLOQUINE; N (2 AMINOETHYL) 7 CHLOROQUINOLIN 4 AMINE; N (3 AMINOPROPYL) 7 CHLOROQUINOLIN 4 AMINE; N (4 AMINOBUTYL) 7 CHLOROQUINOLIN 4 AMINE; N (5 AMINOPENTAN 2 YL) 6 METHOXYQUINOLIN 8 AMINE; N [2 [(7 CHLOROQUINOLIN 4 YL)AMINO]BUTYL]CARBAMOYLFERROCENE; N [2 [(7 CHLOROQUINOLIN 4 YL)AMINO]ETHYL]CARBAMOYLFERROCENE; N [2 [(7 CHLOROQUINOLIN 4 YL)AMINO]PHENYL]CARBAMOYLFERROCENE; N [2 [(7 CHLOROQUINOLIN 4 YL)AMINO]PROPYL]CARBAMOYLFERROCENE; N [4 [(6 METHOXYQUINOLIN 8 YL)AMINO]PENTYL]CARBAMOYLFERROCENE; PRIMAQUINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIMALARIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHO CELL; CYTOTOXICITY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SENSITIVITY; DRUG SYNTHESIS; FEMALE; IC 50; MELTING POINT; MOLECULAR WEIGHT; NONHUMAN; PLASMODIUM FALCIPARUM; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

EID: 78049322381     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1296337     Document Type: Article

References (37)

1. Jung M, Li X, Bustos DA, Elsohly HN, McChesney JD, Milhous WK. Synthesis activity of (+)-deoxyartemisinin. J Med Chem. 1990;33:1516-8.
2. Payne D. Did medicated salt hasten the spread of chloroquine resistance in Plasmodium falciparum? Parasitol Today. 1988;4:112-115.
3. nd ed. Academic Press: London, 1987.
4. Cherfas J. Malaria vaccines: the failed promise. Science. 1990;247:402-3.
5. Cowden WB, Halladay PK, Cunningham RB, Hunt NH, Clark IA. Flavins as potential antimalarials. 2. 3-Methyl-10-(substituted-phenyl) flavins. J Med Chem. 1991;34:1818-22.
6. Dubar F, Anquetin G, Pradines B, Dive D, Khalife J, Biot C. Enhancement of the antimalarial activity of ciprofloxacin using a double prodrug/biorganometallic approach. J Med Chem. 2009;52:7954-7.
7. Gao LM, Hernández R, Matta J, Meléndez E. Synthesis, structure, electrochemistry, and cytotoxic properties of ferrocenyl ester derivatives. Met Based Drugs. 2009 March 24. doi: 10.1155/2009/420784. Pub Med Central PMCID: PMC2659881.
8. Osella D, Ferrali M, Zanello P, Laschi F, Fontani M, Carlo N, et al. On the mechanism of the antitumor activity of ferrocenium derivatives. Inorg Chim Acta. 2000;306:42-8.
9. Mokdsi G, Harding MM. Inhibition of human topoisomerase II by the antitumor metallocenes. J Inorg Biochem. 2001;83:205-9.
10. Dombrowski KE, Baldwin W, Sheats JE. Metallocenes in biochemistry, microbiology and medicine. J Organomet Chem. 1986;302:281-306.
11. Togni A, Hayashi T, editors. Ferrocenes: homogeneous catalysis, organic synthesis, materials science. Weinheim (Germany): Wiley-VCH; 1995.
12. Arrayas RG, Adrio J, Carretero JC. Recent applications of chiral ferrocene ligands in asymmetric catalysis. Angew Chem Int Ed. 2006;45:7674-715.
13. Atkinson RCJ, Gibson VC, Long NJ. The syntheses and catalytic applications of unsymmetrical ferrocene ligands. Chem Soc Rev. 2004;33:313-328.
14. Top S, Tang J, Vessières A, Carrez D, Provot C, Jaouen G. Ferrocenyl hydroxytamoxifen: a prototype for a new range of oestradiol receptor site-directed cytotoxics. Chem Commun. 1995:995-6.
15. Motohashi N, Meyer R, Gollapudi SR, Bhattiprolu KR. Synthesis and activity of potential antitumor ferrocenes. J Organomet Chem. 1990;398:205-217.
16. Biot C, François N, Maciejewski L, Brocard J, Poulain D. Synthesis and antifungal activity of a ferrocene-fluconazole analogue. Biorg Med Chem Let. 2000;10:839-41.
17. Itoh T, Shirakami S, Ishida N, Yamashita Y, Yoshid T, Kimb HS, et al. Synthesis of novel ferrocenyl sugars and their antimalarial activities. Biorg Med Chem Let. 2000;10:1657-9.
18. Biot C, Glorian G, Maciejewski LA, Brocard JS, Domarle O, Blampain G, et al. Synthesis and antimalarial activity in vitro and in vivo of a new ferrocene-chloroquine analogue. J Med Chem. 1997;40:3715-8.
19. Chim P, Lim P, Sem R, Nhem S, Maciejewski L, Fandeur L. The in-vitro antimalarial activity of ferrochloroquine measured against Cambodian isolates of Plasmodiumfalciparum. Ann Trop Med Parasitol. 2004;98:419-24.
20. Domarle O, Blampain G, Agnaniet H, Lebibi J, Brocard J, Maciejewski L, et al. In vitro antimalarial activity of a new organometallic analog, ferroquine-chloroquine. Antimicrob Agents Chemother. 1998;42:540-4.
21. http://clinicaltrials.org/ct2/show/NCT00563914.
22. Biot C, Delhaes L, Maciejewski LA, Mortuaire M, Camus D, Dive D, et al. Synthetic ferrocenic mefloquine and quinine analogues as potential antimalarial agents. Eur J Med Chem. 2000;35:707-14.
23. Beagley P, Blaclie MAL, Chibale K, Clarkson C, Meijboom R, Moss JR, et al. Synthesis and antiplasmodial activity in vitro of new ferrocene-chloroquine analogues. Dalton Trans. 2003:3046-51.
24. Top S, Vessières A, Cabestaing C, Laios I, Leclercq G, Provot C, et al. Studies on organometallic selective receptor modulators (SERMs). Dual activity in the hydroxy-ferrocifen series. J Organomet Chem. 2001;637-639:500-6.
25. Wu X, Tiekink ERT, Kostetski I, Kocherginski N, Tan ALC, Khoo SB, et al. Antiplasmodial activity of ferrocenyl chalcones: investigations into the role of ferrocene. Eur J PharmSci. 2006;27:175-87.
26. Biot C, Daher W, Ndiaye CM, Melnyk P, Pradines B, Chavain N, et al. Probing the role of the covalent linkage of ferrocene into a chloroquine template. J Med Chem. 2006;49:4707-17.
27. Gagnon P, Huang Xicai, Therrien E, Keillor JW. Peptide coupling of unprotected amino acids through in situ p-nitrophenyl ester formation. Tetrahedron Let. 2002;43:7717-9.
28. Trager W, Jensen JB. Human malaria parasites in continuous culture. Science. 1976;193:673-6.
29. Makler MT, Ries JM, Williams JA, Bancroft JE, Piper RC, Gibbins BL, et al. Parasite lactate dehydrogenase as an assay for plasmodium falciparum drug sensitivity. Am J Trop Med Hyg. 1993;48:739-42.
30. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983;65:55-63.
31. Rubinstein LV, Shoemaker RH, Paull KD, Simon RM, Tosini S, Skehan P, et al. Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay against a diverse panel of human tumor cell lines. J Natl Cancer Inst. 1990;82:1113-8.
32. Swarts JC, Neuse EW, Lamprecht GJ. Synthesis and characterization of water-soluble polyaspartamide-ferrocene conjugates for biomedical application. J Inorg Organomet Polym. 1994;4:143-53.
33. De D, Krogstad FM, Byers LD, Krogstad DJ. Structure-activity relationships for antiplasmodial activity among 7-substituted 4-aminoquinolines. J Med Chem. 1998;41:4918-26.
34. Biot C, Taramelli D, Forfar-Bares I, Maciejewski LA, Boyce M, Nowogrocki G, Brocard JS, Basilicao N, Olliaro P, Egan TJ. Insights into the mechanism of action of ferroquine. Relationship between physicochemical properties and antiplasmodial activity. Mol Pharm. 2005;2:185-93.
35. Delarue-Cochin S, Grellier P, Maes L, Mouray E, Sergheraet C, Melnyk P. Synthesis and antimalarial activity of carbamate and amide derivatives of 4-anilinoquinoline. Eur J Med Chem. 2008;43:2045-55.
36. Lin C, Feny-yi Q, Yan-chang Z. Field observations on the antimalarial piperaquine. Chin Med J. 1982;95:281-6.
37. Lin C. Recent studies on the antimalarial efficacy of piperaquine and hydroxypiperaquine. Chin Med J. 1991;104:161-4.