Synthesis and antimalarial activity of 11 dispiro-1,2,4,5-tetraoxane analogues of WR 148999. 7,8,15,16-tetraoxadispiro[5.2.5.2]hexadecanes substituted at the 1 and 10 positions with unsaturated and polar functional groups

Journal of Medicinal Chemistry

Volumn 42, Issue 8, 1999, Pages 1477-1480

  Dong, Yuxiang ^a   Matile, Hugues ^b   Chollet, Jacques ^b   Kaminsky, Ronald ^c   Wood, James K ^d   Vennerstrom, Jonathan L ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

^c SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^d UNIVERSITY OF NEBRASKA AT OMAHA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,10 BIS(2 PROPENYL) 7,8,15,16 TETRAOXADISPIRO[5.2.5.2]HEXADECANE; 1,10 BIS(CARBOETHOXYMETHYL) 7,8,15,16 TETRAOXADISPIRO [5.2.5.2]HEXADECANE; 1,10 DIMETHYL 7,8,15,16 TETRAOXADISPIRO[5.2.5.2]HEXADECANE; 11 DISPIRO 1,2,4,5 TETRAOXANE DERIVATIVE; ANTIMALARIAL AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIMALARIAL ACTIVITY; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; MALARIA; NONHUMAN; ORAL DRUG ADMINISTRATION; SHORT SURVEY; SUBCUTANEOUS DRUG ADMINISTRATION;

ADMINISTRATION, ORAL; ALKANES; ANIMALS; ANTIMALARIALS; INJECTIONS, SUBCUTANEOUS; MALARIA; MICE; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; SPIRO COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAOXANES;

EID: 0033594440     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980698f     Document Type: Short Survey

References (26)

1. For recent reviews, see: (a) Jefford, C. W. Peroxidic Antimalarials. Adv. Drug Res. 1997, 29, 271-325.
2. (b) Casteel, D. A. Antimalarial Agents. In Burger's Medicinal Chemistry and Drug Discovery; Wolff, M. E., Ed.; John Wiley & Sons: New York, 1997; Vol. 5, pp 3-91.
3. (c) Cumming, J. N.; Ploypradith, P.; Posner, G. H. Antimalarial Activity of Artemisinin (Qinghaosu) and Related Trioxanes: Mechanism(s) of Action. Adv. Pharmacol. 1997, 37, 2253-297.
4. (d) Meshnick, S. R.; Taylor, T. E.; Kamchonwongpaisan, S. Artemisinin and the Antimalarial Endoperoxides: from Herbal Remedy to Targeted Chemotherapy. Microbiol. Rev. 1996, 301-315.
5. (e) Butler, A. R.; Wu, Y. L. Artemisinin (Qinghaosu): A New Type of Antimalarial Drug. Chem. Soc. Rev. 1992, 21, 85-90.
6. Vennerstrom, J. L.; Fu, H.-N.; Ellis, W. Y.; Ager, A. L., Jr.; Wood, J. K.; Andersen, S. L.; Gerena, L.; Milhous, W. K. Dispiro-1,2,4,5-tetraoxanes: A New Class of Antimalarial Peroxides. J. Med. Chem. 1992, 35, 3023-3027.
7. Vennerstrom, J. L. Unpublished results.
8. (a) Titulaer, H. A. C.; Zuidema, J.; Lugt, C. B. Formulation and Pharmacokinetics of Artemisinin and its Derivatives. Int. J. Pharmaceut. 1991, 69, 83-92.
9. (b) White, N. J. Clinical Pharmacokinetics and Pharmacodynamics of Artemisinin and Derivatives. Trans. R. Soc. Trop. Med. Hyg. 1994, 88, 41-43.
10. (c) Li, Q.-G.; Pegging, J. O.; Fleckenstein, L. L.; Masonic, K.; Heiffer, M. H.; Brewer, T. G. The Pharmacokinetics and Bioavailability of Dihydroartemisinin, Arteether, Artemether, Artesunic Acid and Artelinic Acid in Rats. J. Pharm. Pharmacol. 1998, 50, 173-182.
11. Gibaldi, M. Biopharmaceutics and Clinical Pharmacokinetics, 4th ed.; Lea and Febriger: Philadelphia, 1991; pp 86-87.
12. Although reports of functionalized tetraoxanes are rare in the literature, tetraoxanes containing carboxylic acid, ester, and ketone functional groups are known, (a) Fichter, F.; Lurie, S. Lävulinsäure-äthylester-keton-peroxid. Helv. Chim. Acta 1931, 14, 1445-1448.
13. (b) Pummerer, R.; Ebermayer, G.; Gerlach, K. Über das Lävulinsäure-peroxid aus Kautschuk (XII. Mitteil.). Chem. Ber. 1931, 64, 804-809.
14. (c) White, H. M.; Colomb, H. O., Jr.; Bailey, P. S. Ozonation of 2,5-Diphenylfuran. J. Org. Chem. 1965, 30, 481-486.
15. (d) House, H. O.; Lee, J. H. C.; VanDerveer, D.; Wissinger, J. E. Perhydroazulenes. 5. Preparation of Perhydroazul-9(10)-en-4-one. J. Org. Chem. 1983, 48, 5285-5288.
16. (a) Bladon, P.; McCullough, K. J.; Morgan, A. R.; Nonhebel, D. C.; Pauson, P. L.; White, G. J. Ketone-derived Peroxides. Part IV. Structural Studies of Cyclic Di- and Tri-peroxides Derived from Ketones. J. Chem. Res. (M) 1980, 3701-3716.
17. (b) McCullough, K. J. Unpublished X-ray crystallographic data for 2.
18. McCullough, K. J.; Morgen, A. R.; Nonhebel, D. C.; Pauson, P. L.; White, G. J. Ketone-derived peroxides. Part I. Synthetic Methods. J. Chem. Res. (M), 1980, 0601-0628.
19. (a) Ganeshpure, P. A.; Adam, W. α-Hydroxy Hydroperoxides (Perhydrates) as Oxygen Transfer Agents in Organic Synthesis. Synthesis 1998, 179-188.
20. (b) Kharasch, M. S.; Sosnovsky, G. Structure of Peroxides Derived from Cyclohexanone and Hydrogen Peroxide. J. Org. Chem. 1958, 23, 1322-1326.
21. Dong, Y.; Vennerstrom, J. L. Dispiro-1,2,4,5-Tetraoxanes via Ozonolysis of Cycloalkanone O-Methyl Oximes: A Comparison with the Peroxidation of Cycloalkanones in Acetonitrile-Sulfuric Acid Media. J. Org. Chem. 1998, 63, 8582-8585.
22. Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. The Enamine Alkylation and Acylation of Carbonyl Compounds. J. Am. Chem. Soc. 1963, 85, 207-221.
23. Findlay, J. A.; Desai, D. N.; Macaulay, J. B. Thermally induced crossed aldol condensations. Can. J. Chem. 1981, 59, 3303-3304.
24. 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.
25. 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.
26. 50 in studies of drug resistance in malaria parasites. Acta Trop. 1993, 55, 257-261.