Structure-activity relationships for antiplasmodial activity among 7- substituted 4-aminoquinolines

Journal of Medicinal Chemistry

Volumn 41, Issue 25, 1998, Pages 4918-4926

  De, Dibyendu ^a   Krogstad, Frances M ^a   Byers, Larry D ^b   Krogstad, Donald J ^a  

^a TULANE UNIVERSITY   (United States)

^b Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOQUINOLINE DERIVATIVE; BROMINE DERIVATIVE; CHLORINE DERIVATIVE; CHLOROQUINE; FLUORINE DERIVATIVE; IODINE DERIVATIVE; PRIMAQUINE; TAFENOQUINE;

ANTIMALARIAL ACTIVITY; ARTICLE; BROMINATION; CHLORINATION; CONTROLLED STUDY; DRUG SYNTHESIS; FLUORINATION; IODINATION; MALARIA FALCIPARUM; NONHUMAN; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION;

AMINOQUINOLINES; ANIMALS; ANTIMALARIALS; CHLOROQUINE; DRUG RESISTANCE; INHIBITORY CONCENTRATION 50; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032481004     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980146x     Document Type: Article

References (59)

1. (a) World Health Report 1995 - Bridging the Gaps; World Health Organization, Geneva Report, May 2, 1995.
2. (b) Miller, L. H.; Good, M. F.; Milon, G. Malaria Pathogenesis. Science 1994, 264, 1878-1884.
3. (c) Malaria: Obstacles and Opportunities; Oaks, S. C., Jr., Mitchell, V. S., Pearson, G. W., Carpenter, C. C., Eds.; Institute of Medicine: Washington, DC; 1991.
4. For general articles and further information on chemistry and biology of antimalarial drugs, see: (a) Murray, M. C.; Perkins, M. E. Chemotherapy of Malaria. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed; Academic Press: San Diego, CA, 1996; pp 141-150. (b) Buss, A. D.; Waigh, R. D. Natural Products as Leads for New Pharmaceuticals. In Burger's Medicinal Chemistry and Drug Discovery; Wolff, M. E., Ed; John Wiley & Sons: New York, 1995; pp 1021-1027. (c) Coatney, G. R.; Cooper, W. C.; Eddy, N. B.; Greenberg, J. Survey of Antimalarials Agents. Chemotherapy of Plasmodium gallinaceum infections, toxicity, correlation of structure and action. Public Health Monograph no. 9: Washington, DC.; 1953.
5. For general articles and further information on chemistry and biology of antimalarial drugs, see: (a) Murray, M. C.; Perkins, M. E. Chemotherapy of Malaria. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed; Academic Press: San Diego, CA, 1996; pp 141-150. (b) Buss, A. D.; Waigh, R. D. Natural Products as Leads for New Pharmaceuticals. In Burger's Medicinal Chemistry and Drug Discovery; Wolff, M. E., Ed; John Wiley & Sons: New York, 1995; pp 1021-1027. (c) Coatney, G. R.; Cooper, W. C.; Eddy, N. B.; Greenberg, J. Survey of Antimalarials Agents. Chemotherapy of Plasmodium gallinaceum infections, toxicity, correlation of structure and action. Public Health Monograph no. 9: Washington, DC.; 1953.
6. For general articles and further information on chemistry and biology of antimalarial drugs, see: (a) Murray, M. C.; Perkins, M. E. Chemotherapy of Malaria. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed; Academic Press: San Diego, CA, 1996; pp 141-150. (b) Buss, A. D.; Waigh, R. D. Natural Products as Leads for New Pharmaceuticals. In Burger's Medicinal Chemistry and Drug Discovery; Wolff, M. E., Ed; John Wiley & Sons: New York, 1995; pp 1021-1027. (c) Coatney, G. R.; Cooper, W. C.; Eddy, N. B.; Greenberg, J. Survey of Antimalarials Agents. Chemotherapy of Plasmodium gallinaceum infections, toxicity, correlation of structure and action. Public Health Monograph no. 9: Washington, DC.; 1953.
7. (d) Krogstad, D. J.; De, D. Chloroquine: Modes of Action and Resistance, and The Activity of Chloroquine Analogues. In Malaria: Parasite Biology, Pathogenesis, and Protection; Sherman, I. W., Ed.; ASM Press: Washington, DC, 1998; pp 331-339.
8. Bloland, P. B.; Lackritz, E. M.; Kazembe, P. N.; Were, J. B.; Steketee, R.; Campbell, C. C. Beyond Chloroquine: Implications of Drug Resistance for Evaluating Malaria Therapeutic Efficacy and Treatment Policy in Africa. J. Infect Dis. 1993, 167, 932-937.
9. (a) Kinnamon, K. E.; Rothe, W. E. Biological screening in the U.S. Army Antimalarial Drug Development Program. Am. J. Trop. Med. Hyg. 1975, 24, 174-178.
10. (b) Berliner, R. W.; Earle, D. P., Jr.; Taggart, J. V.; Zubrod, C. G.; Welch, W. L.; Conan, N. J.; Bauman, E.; Scudder, S. T.; Shannon, J. A. Studies on the Chemotherapy of the Human Malarias. VI. The Physiological Disposition, Antimalarial Activity, and Toxicity of several Derivatives of 4-aminoquinoline. J. Clin. Invest. 1948, 27, 98-107.
11. (c) Andersag, H.; Breitner, S.; Jung, H. Quinoline compounds. US 2,233,970; Chem. Abstr. 1941, 35, 3771.
12. (c) Andersag, H.; Breitner, S.; Jung, H. Quinoline compounds. US 2,233,970; Chem. Abstr. 1941, 35, 3771.
13. (d) Andersag, H.; Breitner, S.; Jung, H. Ger 683,692; Chem. Abstr. 1942, 36, 4973.
14. (d) Andersag, H.; Breitner, S.; Jung, H. Ger 683,692; Chem. Abstr. 1942, 36, 4973.
15. (a) 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, 579-583.
16. th American Society of Tropical Medicine and Hygiene Annual Meeting, San Antonio, Nov 21, 1995. Abstr. No. 594.
17. (c) Krogstad, D. J.; De, D. Chloroquine analogues, their Preparation, and Methods of Preventing and Treating Plasmodial Diseases. PCT Int. Appl. WO 96 40138, 1995; Chem Abstr. 1997, 126, 113160r.
18. (c) Krogstad, D. J.; De, D. Chloroquine analogues, their Preparation, and Methods of Preventing and Treating Plasmodial Diseases. PCT Int. Appl. WO 96 40138, 1995; Chem Abstr. 1997, 126, 113160r.
19. Smart, B. E. Physical and Physicochemical Properties. In Chemistry of Organic Fluorine Compounds II; Hudlicky, M., Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995; pp 979-1003.
20. O'Neill, P. M.; Harrison, A. C.; Storr, R. C.; Hawley, S. R.; Ward, S. A.; Park, B. K. The Effect of Fluorine Substitution on the Metabolism and Antimalarial Activity of Amodiaquine. J. Med. Chem. 1994, 37, 1362-1370.
21. O'Neill, P. M.; Tingle, M. D.; Mahmud, R.; Storr, R. C.; Ward, S. A.; Park, B. K. The Effect of Fluorine Substitution on the Haemotoxicity of Primaquine. Bio. Med. Chem. Lett. 1995, 20, 2309-2314.
22. (a) Grigorov, M.; Weber, J.; Tronchet, J. M.; Jefford, C. W.; Milhous, W. K.; Marie, D. A QSAR study of the antimalarial activity of some synthetic 1,2,4-trioxanes. J. Chem. Inf. Comput. Sci. 1997, 37, 124-130.
23. (b) Fleck, S. L.; Robinson, B. L.; Peters, W. The chemotherapy of rodent malaria. LIV. Combinations of 'Fenozan B07' (Fenozan-50F), a difluorinated 3,3′-spirocyclopentane 1,2,4-trioxane, with other drugs against drug-sensitive and drug-resistant parasites. Ann. Trop. Med. Parasitol. 1997, 91, 33-39.
24. (c) Fleck S. L.; Robinson, B. L.; Peters, W.; Thevin, F.; Boulard, Y.; Glenat, C.; Caillard, V.; Landau, I. The chemotherapy of rodent malaria. LIII. 'Fenozan B07' (Fenozan-50F), a difluorinated 3,3′-spirocyclopentane 1,2,4-trioxane: comparison with some compounds of the artemisinin series. Ann. Trop. Med. Parasitol. 1997, 91, 25-32.
25. (d) Peters, W.; Robinson, B. L.; Tovey, G.; Rossier, J. C.; Jefford, C. W. The chemotherapy of rodent malaria. L. The activities of some synthetic 1,2,4-trioxanes against chloroquine-sensitive and chloroquine-resistant parasites. Part 3: Observations on 'Fenozan-50F', a difluorinated 3, 3′-spirocyclopentane 1,2,4-trioxane. Ann. Trop. Med. Parasitol. 1993, 87, 111-123.
26. (e) Pu, Y. M.; Torok, D. S.; Ziffer, H. Synthesis and Antimalarial Activities of Several Fluorinated Artemisinin Derivatives. J. Med. Chem. 1995, 38, 4120-4124.
27. Posner, G. H.; McGarvey, D. J.; Oh, C. H.; Kumar, N.; Meshnick, S. R.; Asawamahasadka, W. Structure - activity Relationships of Lactone Ring-opened Analogues of the Antimalarial 1,2,4-Trioxane Artemisinin. J. Med. Chem. 1995, 38, 607-612.
28. (a) Collins, W. E.; Jeffery, G. M. Primaquine Resistance in Plasmodium vivax. Am. J. Trop. Med. Hyg. 1996, 55, 243-249 and references therein,
29. (b) Fryauff, D. J.; Baird, J. K.; Basri, H.; Wiady, I.; Purnomo; Bangs, M. J.; Subianto, B.; Harjosuwarno, S.; Tjitra, E.; Richie, T. L.; Hoffman, S. L. Halofantrine and Primaquine for radical Cure of malaria in Irian Jaya, Indonesia. Ann. Trop. Med. Parasitol. 1997, 91, 7-16.
30. (c) Idowu, O. R.; Peggins, J. O.; Brewer, T. G.; Kelly, C. Metabolism of a candidate 8-aminoquinoline antimalarial agent, WR 238605 by rat liver microsomes. Drug Metab. Dispos. 1995, 23, 1-17.
31. (d) Hansch, C.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; John Wiley & Sons: New York, 1979; pp 13-17.
32. (a) De, D.; Byers, L. D.; Krogstad, D. J. Antimalarials: Synthesis of 4-Aminoquinolines that Circumvent Drug Resistance in Malaria Parasites. J. Heterocyclic Chem. 1997, 34, 315-320.
33. (b) De, D.; Mague, J. T.; Byers, L. D.; Krogstad, D. J. Synthesis of (E)-2-(4,7-Dichloroquinolin-2-yl)-3-(dimethylamino)-2-propene-1-al and its use as a Synthetic Intermediate. Tetrahedron Lett. 1995, 36, 205-208.
34. (a) Price, C. C.; Roberts, R. M. The Synthesis of 4-Hydroxyquinolines. I. Through ethoxymethylenemalonic ester. J. Am. Chem. Soc. 1946, 68, 1204-1208.
35. (b) Counsell, R. E.; Pocha, P.; Ranade, V. V.; Sterngold, J.; Beierwaltes, W. H. Tumor Localizing Agents. VII. Radioiodinated Quinoline Derivatives. J. Med. Chem. 1969, 12, 232-236.
36. (c) Counsell, R. E.; Pocha, P.; Morales, J. O.; Beierwaltes, W. H. Tumor Localizing Agents III. Radioiodinated Quinoline Derivatives. J. Pharm. Sci. 1967, 56, 1042-1044.
37. (d) Conroy, A. E.; Mosher, H. S.; Whitmore, F. C. Heterocyclic Basic Compounds. XII. 7-Bromo- and 7-Iodo-quinolines. J. Am. Chem. Soc. 1949, 71, 3236-3237.
38. Surrey, A. R.; Cutler, R. A. The Role of Phenol in the Reaction of 4,7-Dichloroquinoline with Novol Diamine. J. Am. Chem. Soc. 1951, 73, 2623-2626.
39. (a) De; D.; Seth, M.; Puri, S. K.; Chandra, S.; Bhaduri, A. P. 3-(Arylmethyl)-1-(3-diethylaminopropyl)pyrrolidines for reversing the chloroquine resistance of chloroquine-resistant Plasmodium species and process for its preparation. Eur. Pat. Appl. EP562185, 1993; Chem. Abstr. 1994, 720, 106757p.
40. (a) De; D.; Seth, M.; Puri, S. K.; Chandra, S.; Bhaduri, A. P. 3-(Arylmethyl)-1-(3-diethylaminopropyl)pyrrolidines for reversing the chloroquine resistance of chloroquine-resistant Plasmodium species and process for its preparation. Eur. Pat. Appl. EP562185, 1993; Chem. Abstr. 1994, 720, 106757p.
41. (b) De, D. Ph.D. Thesis, University of Gorakhpur, Gorakhpur, India, 1990.
42. 19F NMR Chemical-Shift and Relaxation, Optical Absorption, and Fluorescence Studies. Biopolymers 1981, 20, 435-449
43. Everett, T. S. Nuclear Magnetic Resonance Spectroscopy of Organofluorine Compounds. In Chemistry of Organic Fluorine Compounds II; Hudlicky, M., Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995; pp 1037-1086.
44. 10-propargyl-5,8-didi-ethylaminezafolic acid (ICI 198583). J. Med. Chem. 1996, 39, 73-85.
45. (a) Gribble, G. W.; Lord, P. D.; Skotnicki, J.; Dietz, S. E.; Eaton, J. T.; Johnson, J. L. Reactions of Sodium Borohydride in Acidic Media. I. Reduction of Indoles and Alkylation of Aromatic Amines with Carboxylic Acids. J. Am. Chem. Soc. 1974, 96, 7812-7814.
46. (a) Umino, N.; Iwakuma, T.; Itoh, N. Sodium Acyloxyborohydrides as New Reducing Agents. I. Reduction of Carboxamides to the Corresponding Amines. Tetrahedron Lett. 1976, 10, 763-766.
47. (b) Gribble, G. W.; Jasinski, J. M.; Pellicone, J. T.; Panetta, J. A. Synthesis 1978, 766-768.
48. Marchini, P.; Liso, G.; Reho, A. Sodium Borohydride-carboxylic Acid Systems. Useful Reagents for the Alkylation of Amines. J. Org. Chem. 1975, 40, 3453-3456.
49. 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.
50. 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.
51. Teklehaimanot, A.; Nguyen-Dinh, P.; Collins, W. E.; Barber, A. M.; Campbell, C. C. Evaluation of sporontocidal compounds using gametocytes produced in vitro. Am. J. Trop. Med. Hyg. 1985, 34, 429-434.
52. Krogstad, D. J.; Gluzman I. Y.; Herwaldt, B. L.; Schlesinger, P. H.; Wellems T. E. Energy-dependence of Chloroquine Accumulation and Chloroquine Efflux. Biochem. Pharmacol. 1992, 43, 57-62.
53. O'Brien, R. L., Hahn, F. E. Chloroquine Structural Requirements for Binding to Deoxyribonucleic Acid and Antimalarial Activity. Antimicrob. Agents Chemother. 1965, 5, 315-320.
54. Davey, D. G. The Use of Avian Malaria for the Discovery of Drugs Effective in the Treatment and Prevention of Malaria: I. Drugs for Causal Prophylaxis and Radical Cure or the Chemotherapy of Exo-erythrocytic Forms. Ann. Trop. Med. Parasitol. 1946, 40, 453-471.
55. Peters, W. Chemotherapy of Malaria. In Malaria; Kreir, J. P., Ed.; Academic Press: New York, 1980; Vol. 1, pp 145-283.
56. Krogstad, D. J.; Gluzman, I. Y.; Kyle, D. E.; Oduola, A. M. J.; Martin, S. K.; Milhous, W. K.; Schlesinger, P. H. Efflux of Chloroquine from Plasmodium falciparum: Mechanism of Chloroquine Resistance. Science 1987, 238, 1283-1285.
57. Bray, P. G.; Howells, R. E.; Ritchie, G. Y.; Ward, S. A. Rapid Chloroquine Efflux Phenotype in Both Chloroquine-sensitive and Chloroquine-resistant Plasmodium falciparum: A Correlation of Chloroquine Sensitivity with Energy-dependent Drug Accumulation. Biochem. Pharmacol. 1992, 44, 1317-1324.
58. Su X.-Z.; Kirkman, L. A.; Fujioka, H.; Wellems, T. E. Complex Polymorphisms in a ∼330 kDa Protein are Linked to Chloroquine-resistant Plasmodium falciparum in Southeast Asia and Africa. Cell 1997, 97, 591-603.
59. King, T. C.; Schlesinger, D.; Krogstad, D. J. The Assessment of Drug Combinations. Rev. Infect. Dis. 1981, 3, 627-633.