Synthesis and antimalarial activity of heteroatom-containing bicyclic endoperoxides

Tetrahedron

Volumn 53, Issue 1, 1997, Pages 37-50

  Posner, Gary H ^a   González, Lluïsa ^a   Cumming, Jared N ^a   Klinedinst, Donna ^b   Shapiro, Theresa A ^b  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; ARTEMISININ; ARTEMISININ DERIVATIVE; CHLOROQUINE; ENDOPEROXIDE;

ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NORMAL HUMAN; NUCLEAR MAGNETIC RESONANCE; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 12444296964     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00975-1     Document Type: Article

References (44)

1. Casteel, D. A. Natural Prod. Reports 1992, 289.
2. Capon, R. J. in Studies in Natural Products Chemistry, Atta-ur-Rahman, Ed., Elsevier Science, Amsterdam, 1991, Vol. 9, pp 15-33.
3. Samuelsson, B. J. Am. Chem. Soc. 1965, 87, 3011.
4. Hahmberg, M.; Samuelsson, B. Proc. Natl. Acad. Sci. USA 1973, 70, 899.
5. Nugteren, D. H.; Hazelhof, E. Biochim. Biophys. Acta 1973, 326, 448.
6. Pace-Asciak, C.; Nashat, M. Biochim. Biophys. Acta 1975, 388, 243.
7. Klayman, D. L. Science 1985, 228, 1049.
8. White, N. J. Trans. R. Soc. Trop. Med. Hyg. 1994, 88 (Suppl. 1), 3.
9. Zhou, W. S.; Xu, X. X. Acc. Chem. Res. 1994, 27, 211.
10. Jung, M. Curr. Med. Chem. 1994, 1, 46.
11. McCullough, K. J. Contemp. Org. Syn. 1995, 2, 225.
12. See also, Avery, M. A.; Gao, F.; Chong, W. K. M.; Hendrickson, T. F.; Inman, W. D.; Crews, P. Tetrahedron 1994, 50, 9547.
13. Meshnick, S. R.; Taylor, T. E.; Kamchonwongpaisan, S. Microbiol. Rev. 1996, 60, 301.
14. Cumming, J. N.; Ploypradith, P.; Posner, G. H. Adv. Pharmacol. 1996, 37, 253.
15. Boukouvalas, J.; Pouliot, R.; Fréchette, Y. Tetrahedron Lett. 1995, 35, 4167.
16. Jiang, H.-L.; Chen, K.-X.; Tang, Y.; Chen, J.-Z.; Ji, R.-Y. Chinese J. Chem. 1995, 13, 131.
17. Singh, C.; Misra, D.; Saxena, G.; Chandra, S. Bioorg. Med. Chem. Lett. 1995, 5, 1913.
18. Venugopalan, B.; Bapat, C. P.; Karnik, P. J.; Catterjee, D. K.; Iyer, N.; Lepcha, D. J. Med. Chem. 1995, 38, 1922.
19. Jefford, C. W.; Kohmoto, S.; Jaggi, D.: Timári, G.; Rossier, J.-C.; Rudaz, M.; Barbuzzi, O.; Gérard, D.; Burger, U.; Kamalaprija, P.; Mareda, J.; Bernardinelli, G.; Manzanares, I.; Canfield, C. J.; Fleck, S. L.; Robinson, B. L.; Peters, W. Helv. Chim. Acta 1995, 78, 647.
20. Posner, G. H.; McGarvey, D. J.; Oh, C. H.; Kumar, N.; Meshnick, S. R.; Asawamahasakda, W. J. Med. Chem. 1995, 38, 607.
21. Posner, G. H.; Oh, C. H.; Gerena, L.; Milhous, W. K. Heteroatom Chem. 1995, 6, 105.
22. Avery, M. A.; Fan, P.; Karle, J. M.; Bank, J. D.; Miller, R.; Goins, D. K. J. Med. Chem. 1996, 39, 1885.
23. de Almeida Barbosa, L.-C.; Cutler, D.; Mann, J.; Crabbe, M. J.; Kirby, G. C.; Warhurst, D. C. J. Chem. Soc., Perkin Trans. 1 1996, 1101.
24. Pine, S. H. Org. Reactions 1993, 43, 1.
25. For methylenation of a β-bromoketone, see Winkler, J. D.; Muller, C. L.; Scott, R. D. J. Am. Chem. Soc. 1988, 101, 4831.
26. For methylenation of a α-selenoketone, see Burnier, G.; Schwager, L.; Vogel, P. Helv. Chim. Acta 1986, 69, 1310.
27. For a recent report with reading references, see Griesbeck, A. G.; Sadlek, O.; Polborn, K. Liebigs Ann. 1996, 545.
28. Balci, M.; Saracoglu, N.; Menzek, A. Tetrahedron Lett. 1996, 37, 921.
29. Adam, W.; Duran, N. J. Chem. Soc. Chem. Comm. 1972, 798.
30. Posner, G. H.; Wang, D. W.; González, L.; Tao, X.; Cumming, J. N.; Klinedinst, D.; Shapiro, T. A. Tetrahedron Lett. 1996, 37, 815.
31. Posner, G. H.; Cumming, J. N.; Ploypradith, P.; Oh, C. H. J. Am. Chem. Soc. 1995, 117, 5885.
32. Jeon, Y.T.; Lee, C.-P.; Mariano, P.S. J. Am. Chem. Soc. 1991, 113, 8847.
33. Haynes, R.K.; Vonwiller, S.C. Tetrahedron Lett., 1996, 37, 253 and 257.
34. Jefford, C.W.; Vicente, M.G.H.; Jacquier, Y.; Favarger, F.; Maredo, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chim. Acta, 1996, 79, 1475.
35. Ponnudurai, T.; Leeuwenberg, A. D. E. M.; Meuwissen, J. H. E. T. Trop. Geogr. Med. 1981, 33, 50.
36. Tebbe, F.N.; Parshall, G.W.; Reddy, G.S. J. Am. Chem. Soc. 1978, 100, 3611.
37. Gajda, T.; Zwierzak, A. Synthesis 1981, 1005.
38. Takahashi, Y.; Okitsu, O.; Ando, M.; Miyashi, T. Tetrahedron Lett. 1994, 35, 3953.
39. Harpp, D.N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737.
40. Miyahara, Y. J. Heterocyclic Chem. 1979, 16, 1147.
41. Trost, B.M.; Curran, D.P. Tetrahedron Lett. 1981, 22, 1287.
42. Desjardins, R. E.; Canfield, C. J.; Haynes, J. D.; Chulay, J. D. Antimicrob. Agents Chemother. 1979, 16, 710.
43. Milhous, W. K.; Weatherly, N. F.; Bowdre, J. H.; Desjardins, R. Antimicrob. Agents Chemother. 1985, 27, 525.
44. Bard, Y. Nonlinear Parameter Estimation; Academic Press: New York, 1974; p 94.