Bisquinolines. 2. Antimalarial N,N-Bis(7-chloroquinolin-4- yl)heteroalkanediamines

Journal of Medicinal Chemistry

Volumn 41, Issue 22, 1998, Pages 4360-4364

  Vennerstrom, Jonathan L ^a   Ager Jr , Arba L ^b   Dorn, Arnulf ^d   Andersen, Steven L ^c   Gerena, Lucia ^c   Ridley, Robert G ^d   Milhous, Wilbur K ^c  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b UNIVERSITY OF MIAMI MILLER SCHOOL OF MEDICINE   (United States)

^c WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

^d F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

7 CHLOROQUINOLINE DERIVATIVE; ANTIMALARIAL AGENT; CHLOROQUINE; HEMATIN; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTIMALARIAL ACTIVITY; ARTICLE; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; MALARIA; MOUSE; NONHUMAN; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM;

ANIMALS; ANTIMALARIALS; BIOPOLYMERS; HEMIN; MALARIA; MALE; MICE; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032561218     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9803828     Document Type: Article

References (33)

1. Basco, L. K.; Ruggeri, C.; LeBras, J. Molécules Antipaludiques; Masson: Paris, 1994; pp 115-120.
2. Vennerstrom, J. L.; Ellis, W. Y.; Ager, A. L., Jr.; Andersen, S. L.; Gerena, L.; Milhous, W. K. Bisquinolines. 1. N,N Bis(7- chloroquinolin-4-yl)alkanediamines With Potential Against Chloroquine-Resistant Malaria. J. Med. Chem. 1992, 35, 2129-2134.
3. Dorn, A.; Vippagunta, S. R.; Matile, H.; Bubendorf, A.; Vennerstrom, J. L.; Ridley, R. G. A Comparison and Analysis of Several Ways to Promote Haematin (Haem) Polymerisation and an Assessment of its Initiation In Vitro. Biochem. Pharmacol. 1998, 55, 737-747.
4. (a) Slater, A. F. G. Chloroquine: Mechanism of Drug Action and Resistance in Plasmodium falciparum. Pharmacol. Ther. 1993, 57, 203-235.
5. (b) Dorn, A.; Stoffel, R.; Matile, H,; Bubendorf, A.; Ridley, R. G. Malarial Haemozoin/β-Haematin Supports Haem Polymerization in the Absence of Protein. Nature 1995, 374, 269-271.
6. (c) Sullivan, D. J., Jr.; Gluzman, I. Y.; Russel, D. G.; Goldberg, D. E. On the Molecular Mechanism of Chloroquine's Antimalarial Action. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 11865-11870.
7. (d) Chou, A. C.; Fitch, C. D. Control of Heme Polymerase by Chloroquine and Other Quinoline Derivatives. Biochem.. Biophys. Res. Commun. 1993, 195, 422-427.
8. Basco, L. K.; Andersen, S. L.; Milhous, W. K.; LeBras, J.; Vennerstrom, J. L. In Vitro Activity of Bisquinoline WR268,- 668 Against African Clones and Isolates of Plasmodium falciparum. Am. J. Trop. Med. Hyg. 1994, 50, 200-205.
9. 2-Bis(7-Chloroquinolin-4-yl)Cyclohexane- 1,2-Diamine: Comparison of Two Stereoisomers and Detailed Evaluation of the S,S Enantiomer, Ro 47-7737. Antimicrob. Agents Chemother. 1997, 41, 677-686.
10. Raynes, K.; Galatis, D.; Cowman, A. F.; Tilley, L.; Deady, L. W. Synthesis and Activity of Some Antimalarial Bisquinolines. J. Med. Chem. 1995, 38, 204-206.
11. Ismail, F. M. D.; Dascombe, M. J.; Carr, P.; North, S. E. An Exploration of the Structure-activity Relationships of 4-Aminoquinolines: Novel Antimalarials with Activity In-vivo. J. Pharm. Pharmacol. 1996, 48, 841-850.
12. Cowman, A. F.; Deady, L. W.; Deharo, E.; Desneves, J.; Tilley, L. Synthesis and Activity of Some Antimalarial Bisquinolinemethanols. Aust. J. Chem. 1997, 50, 1091-1096.
13. Raynes, K.; Foley, M.; Tilley, L.; Deady, L. W. Novel Bisquinoline Antimalarials. Biochem. Pharmacol. 1996, 52, 551-559.
14. Tyman, J.; Ghorbanian, S.; Muir, M.; Tychopoulous, V.; Bruce, I.; Fisher, I. Improved Nucleophilic Displacements in N-Methylpyrrolidinone as a Solvent. Synth. Commun. 1989, 19, 179-188.
15. Singh, T.; Stein, R. G.; Hoops, J. F.; Biel, J. H.; Hoya, W. K.; Cruz, D. R. Antimalarials. 7-Chloro-4-(substituted amino)- quinolines. J. Med. Chem. 1971, 14, 283-286.
16. (a) Bray, P. G.; Hawley, S. R.; Ward, S. A. 4-Aminoquinoline Resistance of Plasmodium falciparum: Insights from the Study of Amodiaquine Uptake. Mol. Pharmacol. 1996, 50, 1551-1558.
17. (b) Martiney, J. A.; Cerami, A.; Slater, A. F. G. Verapamil Reversal of Chloroquine Resistance in the Malaria Parasite Plasmodium falciparum Is Specific for Resistant Parasites and Independent of the Weak Base Effect. J. Biol. Chem. 1995, 270, 22393-22398.
18. + Exchanger Determines Chloroquine Uptake in Plasmodium falciparum. J. Cell. Biol. 1998, 140, 335-345.
19. 50 values.
20. (a) Ridley, R. G.; Hofheinz, W.; Matile, H.; Jaquet, C.; Dorn, A.; Masciadri, R.; Jolidon, S.; Richter, W. F.; Guenzi, A.; Girometta, M.-A.; Urwyler, H.; Huber, W.; Thaithong, S.; Peters, W. 4-Aminoquinoline Analogs of Chloroquine with Shortened Side Chains Retain Activity against Chloroquine-Resistant Plasmodium falciparum. Antimicrob. Agents Chemother. 1996, 40, 1846-1854.
21. (b) Geary, T. G.; Divo, A. A.; Jensen, J. B. Activity of Quinoline-Containing Antimalarials Against Chloroquine- Sensitive and -Resistant Strains of Planmodium falciparum In Vitro. Trans. R. Soc. Trop. Med. Hyg. 1987, 82, 499-503.
22. (c) Aderounmu, A. F. In Vitro Assessment of the Antimalarial Activity of Chloroquine and its Major Metabolites. Ann. Trop. Med. Parasitol. 1984, 78, 581-585.
23. (a) Hawley, S. R.; Bray, P. G.; Park, B. K.; Ward, S. A. Amodiaquine Accumulation in Plasmodium falciparum as a Possible Explanation for its Superior Antimalarial Activity Over Chloroquine. Mol. Biochem, Parasitol. 1996, 80, 15-25.
24. 3H]- Chloroquine by Drug-Sensitive and -Resistant Strains of the Human Malaria Parsite Plasmodium falciparum. Biochem. Pharmacol. 1986, 35, 3805-3812.
25. 3H- Chloroquine. Am. J. Pathol. 1972, 67, 277-284.
26. Hawley, S. R.; Bray, P. G.; Mungthin, M.; Atkinson, J. D.; O'Neill, P. M.; Ward, S. A. Relationship Between Antimalarial Drug Activity, Accumulation, and Inhibition of Heme Polymerisation in Plasmodium falciparum. In Vitro. Antimicrob. Agents Chemother. 1998, 42, 682-686.
27. Dorn, A.; Vippagunta, S. R.; Matile, H.; Jaquet, C.; Vennerstrom, J. L.; Ridley, R. G. An Assessment of Drug-Haematin Binding as a Mechanism for Inhibition of Haematin Polymerisation by Quinoline Antimalarials. Biochem. Pharmacol. 1998, 55, 727-736.
28. Scott, M. D.; Yang, L.; Ulrich, P.; Shupe, T. Pharmacologic Interception of Heme: A Potentials Therapeutic Strategy for the Treatment of β Thalassemia? Redox Rep. 1997, 3, 159-167.
29. Singh, S.; Puri, S. K.; Singh, S. K.; Srivastava, R.; Gupta, R. C.; Pandey, V. C. Characterization of Simian Malarial Parasite (Plasmodium knowleni)-Induced Putrescine Transport in Rhesus Monkey Erythrocytes. J. Biol. Chem. 1997, 272, 13506-13511.
30. Desjardins, R. E.; Canfield, C. J.; Haynes, J. D.; Chulay, J. D. Quantitative Assessment of Antimalarial Activity In Vitro by a Semiautomated Microdilution Technique. Antimicrob. Agents Chemother. 1979, 16, 710-718.
31. Milhous, W. K.; Weatherly, N. F.; Bowdre, J. H.; Desjardins, R. E. In Vitro Activities of and Mechanisms of Resistance to Antifol Antimalarial Drugs. Antimicrob. Agents Chemother. 1985, 27, 525-530.
32. Oduola, A. M. J.; Weatherly, N. F.; Bowdre, J. H.; Desjardins, R. E. Plasmodium. falciparum.: Cloning by Single-Erythrocyte Micromanipulation and Heterogeneity In Vitro. Exp. Parasitol. 1988, 66, 86-95.
33. Ager, A. L., Jr. Rodent Malaria Models. In Handbook of Experimental Parsitology: Antimalarial Drugs I; Peters, W., Richards, W. H. G., Eds.; Springer-Verlag: Berlin, 1984; pp 226-227.