Incorporation of an intramolecular hydrogen-bonding motif in the side chain of 4-aminoquinolines enhances activity against drug-resistant P. falciparum

Journal of Medicinal Chemistry

Volumn 49, Issue 15, 2006, Pages 4535-4543

  Madrid, Peter B ^a   Liou, Ally P ^b   DeRisi, Joseph L ^b   Guy, R Kiplin ^a,b,c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c ST JUDE CHILDREN S RESEARCH HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOQUINOLINE DERIVATIVE; ALKYL GROUP; ALPHA AMINOCRESOL; AMODIAQUINE; ANTIMALARIAL AGENT; AROMATIC COMPOUND; BIALAMICOL; CHLOROQUINE; CRESOL; HALOFANTRINE; MEFLOQUINE; SN 7744; UNCLASSIFIED DRUG;

ALKALINITY; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; COST EFFECTIVENESS ANALYSIS; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HYDROGEN BOND; IC 50; MULTIDRUG RESISTANCE; NONHUMAN; PKA; PLASMODIUM FALCIPARUM; STEREOCHEMISTRY;

AMINOQUINOLINES; ANIMALS; ANTIMALARIALS; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG RESISTANCE; HYDROGEN BONDING; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33746748754     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0600951     Document Type: Article

References (29)

1. Baird, J. K. Effectiveness of antimalarial drugs. N. Engl. J. Med. 2005, 352 (15), 1565-1577.
2. Sachs, J.; Malaney, P. The economic and social burden of malaria. Nature 2002, 415 (6872), 680-685.
3. Sidhu, A. B.; Verdier-Pinard, D.; Fidock, D. A. Chloroquine resistance in Plasmodium falciparum malaria parasites conferred by pfcrt mutations. Science 2002, 298 (5591), 210-213.
4. Price, R. N.; Uhlemann, A.-C.; Brockman, A.; McGready, R.; Ashley, E.; Phaipun, L.; Patel, R.; Laing, K.; Looareesuwan, S.; White, N. J. Mefloquine resistance in Plasmodium falciparum and increased pfmdr1 gene copy number. Lancet 2004, 364 (9432), 438-447.
5. 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 (8), 1846-1854.
6. De, D.; Krogstad, F. M.; Cogswell, F. B.; Krogstad, D. J. Aminoquinolines that circumvent resistance in Plasmodium falciparum in vitro. Am. J. Trop. Med. Hyg. 1996, 55 (6), 579-583.
7. Madrid, P. B.; Sherrill, J.; Liou, A. P.; Weisman, J. L.; Derisi, J. L.; Guy, R. K. Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities. Bioorg. Med. Chem. Lett. 2005, 15 (4), 1015-1018.
8. Madrid, P. B.; Wilson, N. T.; DeRisi, J. L.; Guy, R. K. Parallel synthesis and antimalarial screening of a 4-aminoquinoline library. J. Comb. Chem. 2004, 6 (3), 437-442.
9. De, D.; Byers, L. D.; Krogstad, D. J. Antimalarials: synthesis of 4-aminoquinolines that circumvent drug resistance in malaria parasites. J. Heterocycl. Chem. 1997, 34 (1), 315-320.
10. Burckhalter, J. H.; Tendick, F. H.; Jones, E. M.; Holcomb, W. F.; Rawlins, A. L. Aminoalkylphenols as antimalarials. I. Simply Substituted α-aminocresols. J. Am. Chem. Soc. 1946, 68, 1894-1901.
11. Wiselogle, F. Y.; Council, N. R. A Survey of Antimalarial Drugs, 1941-1945; Edwards: Ann Arbor, MI, 1946; p 2.
12. Burckhalter, J. H.; Tendick, F. H.; Jones, E. M.; Jones, P. A.; Holcomb, W. F.; Rawlins, A. L. Aminoalkylphenols as antimalarials. II. (Heterocyclic-amino)-α-amino-o-cresols. The Synthesis of camoquin. J. Med. Chem. 1948, 70, 1363-1373.
13. Hunsicker, L. G. The pharmacology of the antimalarials. A rational approach to the therapy of resistant falciparum malaria. Arch. Intern. Med. 1969, 123 (6), 645-649.
14. Jeffery, G. M.; Collins, W. E.; Skinner, J. C. Antimalarial drug trials on a multiresistant strain of Plasmodium falciparum. Am. J. Trop. Med. Hyg. 1963, 12, 844-850.
15. Moore, D. V.; Lanier, J. E. Observations on two Plasmodium falciparum infections with an abnormal response to chloroquine. Am. J. Trop. Med. Hyg. 1961, 10, 5-9.
16. Rieckmann, K. H.; Trenholme, G. M.; Williams, R. L.; Carson, P. E.; Frischer, H.; Desjardins, R. E. Prophylactic activity of mefloquine hydrodiloride (WR 142490) in drug-resistant malaria. Bull. W. H. O. 1974, 51 (4), 375-377.
17. Veber, D. F.; Johnson, S. R.; Cheng, H. Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 2002, 45 (12), 2615-2623.
18. Evans, J. M.; Fake, C. S.; Hamilton, T. C.; Poyser, R. H.; Showell, G. A. Synthesis and antihypertensive activity of 6,7-disubstituted trans-4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ols. J. Med. Chem. 1984, 27 (9), 1127-1131.
19. Evans, J. M.; Fake, C. S.; Hamilton, T. C.; Poyser, R. H.; Watts, E. A. Synthesis and antihypertensive activity of substituted trans-4-amino-3,4- dihydro-2,2-dimethyl-2H-1-benzopyran-3-ols. J. Med. Chem. 1983, 26 (11), 1582-9.
20. Mungthin, M.; Bray, P. G.; Ridley, R. G.; Ward, S. A. Central role of hemoglobin degradation in mechanisms of action of 4-aminoquinolines, quinoline methanols, and phenanthrene methanols. Antimicrob. Agents Chemother. 1998, 42 (11), 2973-2977.
21. O'Neill, P. M.; Bray, P. G.; Hawley, S. R.; Ward, S. A.; Park, B. K. 4-Aminoquinolines. Past, present, and future: a chemical perspective. Pharmacol. Ther. 1998, 77 (1), 29-58.
22. Foley, M.; Tilley, L. Quinoline antimalarials: mechanisms of action and resistance and prospects for new agents. Pharmacol. Ther. 1998, 79 (1), 55-87.
23. Fidock, D. A.; Nomura, T.; Talley, A. K.; Cooper, R. A.; Dzekunov, S. M.; Ferdig, M. T.; Ursos, L. M.; Sidhu, A. B.; Naude, B.; Deitsch, K. W.; Su, X. Z.; Wootton, J. C.; Roepe, P. D.; Wellems, T. E. Mutations in the P. falciparum digestive vacuole transmembrane protein PfCRT and evidence for their role in chloroquine resistance. Mol. Cell 2000, 6 (4), 861-871.
24. Cooper, R. A.; Hartwig, C. L.; Ferdig, M. T. pfcrt is more than the Plasmodium falciparum chloroquine resistance gene: a functional and evolutionary perspective. Acta Trop. 2005, 94 (3), 170-180.
25. Tran, C. V.; Saier, M. H., Jr. The principal chloroquine resistance protein of Plasmodium falciparum is a member of the drug/metabolite transporter superfamily. Microbiology 2004, 150 (1), 1-3.
26. Martin, R. E.; Kirk, K. The malaria parasite's chloroquine resistance transporter is a member of the drug/metabolite transporter superfamily. Mol. Biol. Evol. 2004, 21 (10), 1938-1949.
27. Wellems, T. E. Transporter of a malaria catastrophe. Nat. Med. 2004, 10 (11), 1169-1171.
28. Johnson, D. J.; Fidock, D. A.; Mungthin, M.; Lakshmanan, V.; Sidhu, A. B.; Bray, P. G.; Ward, S. A. Evidence for a central role for PfCRT in conferring Plasmodium falciparum resistance to diverse antimalarial agents. Mol. Cell 2004, 15 (6), 867-877.
29. Barkan, D.; Ginsburg, H.; Golenser, J. Optimisation of flow cytometric measurement of parasitaemia in plasmodium-infected mice. Int. J. Parasitol. 2000, 30 (5), 649-653.