Molecular electronic properties of a series of 4- quinolinecarbinolamines define antimalarial activity profile

Journal of Medicinal Chemistry

Volumn 39, Issue 23, 1996, Pages 4622-4629

  Bhattacharjee, Apurba K ^a   Karle, Jean M ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; MEFLOQUINE; QUINOLINE DERIVATIVE;

ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ARTICLE; COMPUTER ANALYSIS; CONTROLLED STUDY; HYDROPHOBICITY; LIPOPHILICITY; MALARIA; MOLECULAR MODEL; MOUSE; NONHUMAN; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION; SUBCUTANEOUS DRUG ADMINISTRATION;

ANIMALS; ANTIMALARIALS; ELECTRONS; HYDROGEN BONDING; MICE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PIPERIDINES; PLASMODIUM BERGHEI; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 0029850335     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960358z     Document Type: Article

References (40)

1. Oaks, S. C.; Mitchell, V. S.; Pearson, G. W.; Carpenter, C. C. MALARIA Obstacles and Opportunities; National Academic Press: Washington, DC, 1991; pp 15, 144-168.
2. Oduola, A. M. J.; Omitowoju, G. O.; Gerena, L.; Kyle, D. E.; Milhous, W. K.; Sowunmi, A.; Salako, L. A. Reversal of Mefloquine Resistance with Penfluridol in Isolates of Plasmodium Falciparum from South-West Nigeria. Trans. R. Soc. Trop. Med. Hyg. 1993, 87, 81-83.
3. Sweeney, T. R.; Strube, R. E. Antimalarials. In Burger's Medicinal Chemistry, 4th ed.; Wolf, M. E., Ed.; John Wiley & Sons, Inc.: New York, 1979; pp 333-413.
4. Tracy, J. W.; Webster, L. T. Drugs Used in the Chemotherapy of Protozoal Infections: Malaria. In The Pharmacological Basis of Therapeutics, 9th ed.; Hardman, J. G., Limbird, L. E., Molinoff, P. B., Ruddon, R. W. R., Gilman, A. G., Eds.; McGrawHill: New York, 1995; pp 965-985.
5. Sweeney, T. R.; Strube, R. E. The Present Status of Malaria Chemotherapy: Mefloquine, a Novel Antimalarial. Med. Res. Rev. 1981, 1, 281-301.
6. Palmer, K. J.; Holliday, S. M.; Brogden, R. N. Mefloquine: A Review of its Antimalarial Activity, Pharmacokinetic Parameters and Therapeutic Efficacy. Drugs 1993, 45, 430-475.
7. Ginsburg, H.; Geary, T. G. Current Concepts and New Ideas on the Mechanism of Action of Quinoline Containing Antimalarials. Biochem. Pharmacol. 1987, 36, 1567-1576.
8. Schlesinger, P. H.; Krogstad, D. G.; Herwaldt, B. L. Antimalarial Agents: Mechanism of Chloroquine Resistance. Antimicrob. Agents Chemother. 1988, 32, 793-801.
9. Karle, J. M.; Karle, I. L.; Gerena, L.; Milhous, W. K. Stereo-chemical Evaluation of the Relative Activities of the Cinchona Alkaloids against Plasmodium falciparum. Antimicrob. Agents Chemother. 1992, 36, 1538-1544.
10. Davidson, M. W.; Griggs, B. G.; Bokyn, D. W.; Wilson, W. D. Molecular Structural Effects Involved in the Interaction of Quinolinemethanolamines with DNA. Implications for Antimalarial Action. J. Med. Chem. 1977, 20, 1117-1122.
11. Ginsburg, H.; Demel, R. A. Interactions of Hemin, Antimalarial Drugs and Hemin-Antimalarial Complexes with Phospholipid Monolayers. Chem. Phys. Lipids 1984, 35, 331-347.
12. Lullman-Rauch, R. Drug-Induced Lysosomal Storage Disorders. In Lysosomes in Applied Biology and Therapeutics; Dingle, J. T., Jacques, P. J., Shaw, I. H., Eds.; North Holland Publishing: Amsterdam, 1979; Vol. 6, pp 49-130.
13. Lullman, H.; Plosch, H.; Ziegler, A. Ca Replacement by Cationic Amphiphilic Drugs from Lipid Monolayers. Biochem. Pharmacol. 1980, 29, 2969-2974.
14. Murray, J. S.; Zilles, B. A.; Jayasuriya, K.; Politzer, P. Comparative Analysis of the Electrostatic Potentials of Dibenzofuran and Some Dibenzo-p-dioxins. J. Am Chem. Soc. 1986, 108, 915-918.
15. Bhattacharjee, A. K.; Majumdar, D.; Guha, S. Theoretical Studies on the Conformational properties and Pharmacophoric Pattern of Several Bipyridine Cardiotonics. J. Chem. Soc., Perkin Trans. 2 1992, 805-809.
16. SPARTAN 4.0; Wavefunction, Inc.: Irvine, CA, 1995.
17. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. AM1: A New General Purpose Quantum Mechanical Molecular Model. J. Am. Chem. Soc. 1985, 107, 3902-3909.
18. Oleksyn, B. J.; Lebioda, L.; Sliwinski, J. Crystal Structure Investigation of Mefloquine, A New Potent Antimalarial Drug. In Proceedings of the IIIrd Symposium on Organic Crystal Chemistry; Kaluski, Z., Ed.; University Adam Mickiewicz: Poznan, Poland, 1980; pp 200-204.
19. Karle, J. M.; Karle, I. L. Crystal Structure and Molecular Structure of Mefloquine Methylsulfonate Monohydrate; Implications for a Malaria Receptor. Antimicrob. Agents Chemother. 1991, 35, 2238-2245.
20. Karle, J. M.; Karle, I. L. Structure of the Antimalarial (±)-Mefloquine Hydrochloride. Acta Crystallogr. 1991, C47, 2391-2395.
21. Dixon, R. W.; Leonard, J. M.; Hehre, W. J. A. Continuum Solvation Model for the AM1 Semi-Empirical Method. Israel J. Chem. 1993, 33, 427-434.
22. Cramer, C. J.; Truhlar, D. G. An SCF Solvation Model for the Hydrophobie Effect and Absolute Free Energies of Aqueous Solvation. Science 1992, 256, 213-217.
23. Alagona, G.; Ghio, C. The Role of Electrostatics in Solute-Solvent Interactions. J. Mol. Struct. (THEOCHEM) 1992, 256, 187-216.
24. Luque, F. J.; Gadre, S. R.; Orozco, M.; Bhadane, P. K. SCRF Calculation of the Effect of Hydration on the Topology of the Molecular Electrostatic Potential. J. Phys. Chem. 1993, 97, 9380-9384.
25. Sweeney, T. R. In A Survey of Compounds from the Antimalarial Drug Development Program of the US Army Medical Research and Development Command; Walter Reed Army Institute of Research: Washington, DC, 1991; Vol. 1, pp 1-316.
26. Osdene, T. S.; Russell, P. B.; Rane, L. 2,4,7-Triamino-6-ortho-substituted Arylpteridines. A New Series of Potent Antimalarial Agents. J. Med. Chem. 1967, 10, 431-434.
27. Chien, P. L.; Cheng, C. C. Difference in Antimalarial Activity Between Certain Amino Alcohol Diastereomers. J. Med. Chem. 1976, 19, 170-172.
28. Brasseur, J. M.; Dive, G.; Dehareng, D.; Ghuysen, J. M. Electrostatic Potential Maps at the Quantum Chemistry Level of the Active Sites of the Serine Peptidases, α-Chymotrypsin and Subtilisin. J. Theor. Biol. 1990, 145, 183-198.
29. Lee, Y. S.; Pearlstein, R.; Kador, P. F. Molecular Modeling Studies of Aldose Reductase Inhibitors. J. Med. Chem. 1994, 37, 787-792.
30. Hershko, C.; Theanacho, E. N.; Sipra, D. T.; Peter, H. H.; Dobbin, P.; Hider, R. C. The Effect of N-Alkyl Modification on the Antimalarial Activity of 3-Hydroxypyridin-4-one Oral Iron Chelators. Blood 1991, 77, 637-643.
31. Ohnmacht, C. J.; Patel, A. R.; Lutz, R. E. Antimalarials. 7. Bis-(trifluoromethyr)-α-(2-piperidyl)-4-quinolinemethanols. J. Med. Chem. 1971, 14, 926-928.
32. Wetzel, C. R.; Shanklin, J. R.; Lutz, R. E. Antimalarials. 9. α-(2-Piperidyl)-4-quinolinemethanols Carrying 2-Aroxy and 2-(p-Chloroanilino) Groups. J. Med. Chem. 1973, 16, 528-532.
33. Carroll, F. I.; Blackwell, J. T. Optical Isomers of Aryl-2-piperidylmethanol Antimalarial Agents. Preparation, Optical Purity, and Absolute Stereochemistry. J. Med. Chem. 1974, 17, 210-219.
34. Pinder, R. M.; Burger, A. Antimalarials. II. α-(2-Piperidyl)- and α-(2-Pyridyl)-2-trifluoromethyl-4-quinolinemethanols. J. Med. Chem. 1968, 11, 267-269.
35. Patel, A. R.; Ohnmacht, C. J.; Clifford, D. P.; Crosby, A. S.; Lutz, R. E. Antimalarials. 6. Some New α-Alkylaminomethyl-4-quinolinemethanols. J. Med. Chem. 1971, 14, 198-202.
36. Boykin, D. W., Jr.; Patel, A. R.; Lutz, R. E. Antimalarials. IV. A New Synthesis of α-(2-Pyridyl)- and a-(2-Piperidyl)-2-aryl-4-quinolinemethanols. J. Med. Chem. 1968, 11, 273-277.
37. Loy, M.; Joullié, M. M. Synthesis and Properties of Fluorine-Containing Heterocyclic Compounds. 8. α-(2-Pyridyl)-and α-(2-Piperidyl)-2-(trifluoromethyl)-4-azaphenanthrenemethanols. J. Med. Chem. 1973, 16, 549-552.
38. Koppel, H. Final Report to the Division of Experimental Therapeutics. Walter Reed Army Institute of Research, Washington, DC, 1972; No. DA 49-193-MD-2766.
39. Archives of the Chemical Information System, Division of Experimental Therapeutics, Walter Reed Army Institute of Research, Washington, DC; Data Sheet Nos: AJ15288, AW41831, AW41840, AH95165, BE21726, AW41859, BE21860, BF52182.
40. Olsen, R. E. Final Report Summary to the Division of Experimental Therapeutics, Walter Reed Army Institute of Research, Washington, DC, 1976; No. DA 17-73-C-3160.