124. The deoxygenation and isomerization of artemisinin and artemether and their relevance to antimalarial action

Helvetica Chimica Acta

Volumn 79, Issue 5, 1996, Pages 1475-1487

  Jefford, Charles W ^a   Vicente, Maria G H ^a   Jacquier, Yvan ^a   Favarger, France ^a   Mareda, Jiri ^a   Millasson Schmidt, Patricia ^a   Brunner, Gerhard ^a   Burger, Ulrich ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ARTEMETHER; ARTEMISININ; DEOXYARTEMISININ; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; DRUG STRUCTURE; LIVER MICROSOME; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; RAT;

EID: 0030036928     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.19960790520     Document Type: Article

References (71)

1. C. W. Jefford, S. Kohmoto, D Jaggi, G. Timári, J. C. Rossier, M. Rudaz, O. Barbuzzi, D. Gérard, U. Burger, P. Kamalaprija, J. Mareda, G. Bernardinelli, I. Manzanares, C. J. Canfield, S. L. Fleck, B. L. Robinson, W. Peters, Helv. Chim. Acta 1995, 78, 647; C. W. Jefford, J. A. Velarde, G. Bernardinelli, D. H. Bray, D. C Warhurst, W. K. Milhous, ibid. 1993, 76, 1775.
2. C. W. Jefford, S. Kohmoto, D Jaggi, G. Timári, J. C. Rossier, M. Rudaz, O. Barbuzzi, D. Gérard, U. Burger, P. Kamalaprija, J. Mareda, G. Bernardinelli, I. Manzanares, C. J. Canfield, S. L. Fleck, B. L. Robinson, W. Peters, Helv. Chim. Acta 1995, 78, 647; C. W. Jefford, J. A. Velarde, G. Bernardinelli, D. H. Bray, D. C Warhurst, W. K. Milhous, ibid. 1993, 76, 1775.
3. W. Hofheinz, H. Bürgin, E. Gocke, C. Jaquet, R. Masciadri, G. Schmid, H. Stohler, H. Urwyler, Trop. Med Parasitol. 1994, 45, 261; C. Jaquet, H. R. Stohler, J. Chollet, W. Peters, ibid. 1994, 45, 266.
4. W. Hofheinz, H. Bürgin, E. Gocke, C. Jaquet, R. Masciadri, G. Schmid, H. Stohler, H. Urwyler, Trop. Med Parasitol. 1994, 45, 261; C. Jaquet, H. R. Stohler, J. Chollet, W. Peters, ibid. 1994, 45, 266.
5. a) S. R. Meshnick, C. W. Jefford, G. H. Posner, M. A. Avery, W. Peters, Parasitology Today 1996, 12, 79;
6. b) C. W Jefford, D. Misra, J. C. Rossier, P. Kamalaprija, U. Burger, J. Mareda, G. Bernardinelli, W. Peters, B. L. Robinson, W. K. Milhous, F. Zhang, D. K. Gosser, S. R. Meshnick, in 'Perspectives in Medicinal Chemistry', Eds. B. Testa, E. Kyburz, W. Fuhrer, and R. Giger, Verlag Helvetica Chimica Acta, Basel, 1993, Chapt. 29.
7. W. Peters, B L. Robinson, J. C. Rossier, D. Misra, C. W. Jefford, Ann. Trop. Med. Parasitol. 1993, 87, 9.
8. A. F. G. Slater, A. Cerami, Nature (London) 1992, 355, 167.
9. A. F. G. Slater, W. J. Swiggard, B. R. Orton, W D. Flitter, D. E. Goldberg, A. Cerami, G. B. Henderson, Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 325.
10. D. C. Warhurst, Trans. R. Soc. Trop. Med. Hyg. 1981, 75, 606.
11. S. R. Meshnick, A. Thomas, A. Ranz, C. Xu, H. Pan, Mol. Biochem. Parasitol. 1991, 49, 181.
12. Y. Hong, Y. Zang, S. R. Meshnick, Mol. Biochem. Parasitol. 1994, 63, 121; F. Zhang, D. Gosser, Jr., S. R. Meshnick, Biochem. Pharmacol. 1992, 43, 1805.
13. Y. Hong, Y. Zang, S. R. Meshnick, Mol. Biochem. Parasitol. 1994, 63, 121; F. Zhang, D. Gosser, Jr., S. R. Meshnick, Biochem. Pharmacol. 1992, 43, 1805.
14. S. R. Meshnick, Y. Yang, V. Lima, F. Kuypers, S. Kamchonwongpaisan, Y. Yuthavong, Antimicrob. Agents Chemother 1993, 37, 1108.
15. W. Asawamahasakda, I Ittarat, Y. Pu, H. Ziffer, S. R. Meshnick, Antimicrob. Agents Chemother. 1994, 38, 1854.
16. G. H. Posner, C. H. Oh, D. Wang, L. Gerena, W. K. Milhous, S. R. Meshnick, W. Asawamahasakda, J. Med. Chem. 1994, 37, 1256; G. H. Posner, C. H. Oh, J. Am. Chem. Soc. 1992, 114, 8328; G. H. Posner, C. H. Oh, D. Wang, L. Gerena, W. K. Milhous, S. R. Meshnick, W. Asawamahasakda, J. Med. Chem. 1995, 38, 607.
17. G. H. Posner, C. H. Oh, D. Wang, L. Gerena, W. K. Milhous, S. R. Meshnick, W. Asawamahasakda, J. Med. Chem. 1994, 37, 1256; G. H. Posner, C. H. Oh, J. Am. Chem. Soc. 1992, 114, 8328; G. H. Posner, C. H. Oh, D. Wang, L. Gerena, W. K. Milhous, S. R. Meshnick, W. Asawamahasakda, J. Med. Chem. 1995, 38, 607.
18. G. H. Posner, C. H. Oh, D. Wang, L. Gerena, W. K. Milhous, S. R. Meshnick, W. Asawamahasakda, J. Med. Chem. 1994, 37, 1256; G. H. Posner, C. H. Oh, J. Am. Chem. Soc. 1992, 114, 8328; G. H. Posner, C. H. Oh, D. Wang, L. Gerena, W. K. Milhous, S. R. Meshnick, W. Asawamahasakda, J. Med. Chem. 1995, 38, 607.
19. D. Zhu, B. Huang, Z. Chen, M Yin, Yaoxue Xuebo 1980, 15, 509; China Cooperative Research Group on Qinghaosu and its Derivatives as Antimalarials, J. Tradit. Chin. Med. 1982, 2, 25.
20. D. Zhu, B. Huang, Z. Chen, M Yin, Yaoxue Xuebo 1980, 15, 509; China Cooperative Research Group on Qinghaosu and its Derivatives as Antimalarials, J. Tradit. Chin. Med. 1982, 2, 25.
21. a) C. W. Jefford, F. Favarger, M. G. H. Vicente, Y. Jacquier, Helv. Chim. Acta 1995, 78, 452; b) C. W. Jefford, G. Brunner, U. Burger, in preparation.
22. M. Jung, H. N. ElSohly, E. M. Croom, A. T. McPhail, D. R. McPhail, J. Org. Chem. 1986, 51, 5417
23. X. Xu, J. Zhu, D. Huang, W. Zhou, Tetrahedron 1986, 42, 819.
24. A. Brossi, B. Venugopalan, L. Dominguez Gerpe, H. J. C. Yeh, J. L. Flippen-Anderson, P. Buchs, X. D. Luo, W. K. Milhous, W. Peters, J. Med Chem. 1988, 31, 645.
25. a) X. Luo, H. J. C. Yeh, A. Brossi, Heterocycles 1985, 23, 881; A. J. Lin, D. L. Klayman, J. M. Hoch, J. V. Silverton, C. F. George, J. Org. Chem. 1985, 50, 4504;
26. a) X. Luo, H. J. C. Yeh, A. Brossi, Heterocycles 1985, 23, 881; A. J. Lin, D. L. Klayman, J. M. Hoch, J. V. Silverton, C. F. George, J. Org. Chem. 1985, 50, 4504;
27. b) A J. Lin, A. D. Theoharides, D. L. Klayman, Tetrahedron 1986, 42, 2181
28. A. Bax, R. Freeman, J. Magn. Reson. 1981, 44, 542.
29. W. E. Hull, in 'Two-Dimensional NMR Spectroscopy', 2nd edn., Eds. W R Croasmun and R. M. K. Carlson, VCH, Weinheim, 1994, p. 301.
30. G. E. Martin, A. S. Zektzer, 'Two-Dimensional NMR Methods for Establishing Molecular Connectivity', VCH, Weinheim, 1988, Chapt. 3.
31. D. Neuhaus, M. Williamson, 'The Nuclear Overhauser Effect in Structural and Conformational Analysis', VCH, Weinheim, 1989, pp. 253-305.
32. I. Lee, H. N. ElSohly, E. M Croom, C. D. Hufford, J. Nat. Prod 1989, 52, 337.
33. Z Wei, J. Pan, Y. Li, Planta Med. 1992, 58, 300.
34. J. K. Baker, R. H. Yarber, C. D. Hufford, I. Lee, H. N ElSohly, J. D. McChesney, Biomed. Environ. Mass. Spectrom. 1988, 18, 337.
35. W. Wilker, D. Leibfritz, R. Kerrsebaum, W. Bermel, Magn. Reson. Chem. 1993, 31, 287.
36. J. Drenth, Recl. Trav. Chim. Pays-Bos 1980, 99, 185.
37. C. W. Jefford, J. C. Rossier, J. Boukouvalas, Heterocycles 1989, 28, 673
38. M. J. Adams, in 'Enzyme Mechanisms', Eds. M. I Page and A. Williams, Royal Society of Chemistry, London, 1987, Chapt. 24.
39. V Leskovac, A. D. Theoharides, Comp. Biochem. Physiol., C: Comp. Pharmacol. Toxicol. 1991, 99, 391.
40. C. W Jefford, in 'Advances in Detailed Reaction Mechanisms', Vol.2, 'Mechanisms of Biological Importance', Ed. J. M. Coxon, JAI Press, Inc., Greenwich, CT, USA, 1992, pp. 149-187.
41. C. Wentrup, 'Reactive Molecules', J. Wiley and Sons, New York, 1984, p. 90.
42. A. E. Dorigo, M. A. McCarrick, R. J. Loncharich, K. N. Houk, J. Am. Chem. Soc. 1990, 112, 7508.
43. C. Thomson, M. Cory, M. Zerner, Int. J. Quantum Chem. 1991, 18, 231; G. Bernardinelli, C. W. Jefford, D. Maric, C. Thomson, J. Weber, ibid. 1994, 21, 117; C. W. Jefford, J. Weber, M. Grigorov, C. Thomson, H. U. Suter, D. Maric, unpublished.
44. C. Thomson, M. Cory, M. Zerner, Int. J. Quantum Chem. 1991, 18, 231; G. Bernardinelli, C. W. Jefford, D. Maric, C. Thomson, J. Weber, ibid. 1994, 21, 117; C. W. Jefford, J. Weber, M. Grigorov, C. Thomson, H. U. Suter, D. Maric, unpublished.
45. C. Thomson, M. Cory, M. Zerner, Int. J. Quantum Chem. 1991, 18, 231; G. Bernardinelli, C. W. Jefford, D. Maric, C. Thomson, J. Weber, ibid. 1994, 21, 117; C. W. Jefford, J. Weber, M. Grigorov, C. Thomson, H. U. Suter, D. Maric, unpublished.
46. Qinghaosu Research Group, Sci. Sin. 1980, 23, 380.
47. I. Leban, L. Golic, M. Japelj, Acta Pharm. Jugosl. 1988, 38, 71.
48. P. Brun, B. Waegell, in 'Reactive Intermediates', Plenum Press, New York, 1983, Vol. 3, p. 367, and ref. cit therein.
49. A. J. Bloodworth, A. Shah, Tetrahedron Lett. 1995, 36, 7551.
50. J. J. P. Stewart, Comput. Chem. 1989, 10, 209.
51. J. J. P. Stewart, Comput. Chem. 1989, 10, 221
52. J. J. P Stewart, QCPE 455.
53. M. J S. Dewar, N. Trinajstic, J. Am. Chem. Soc. 1968, 90, 1953; M. J. S. Dewar, N. Trinajstic, J. Chem. Soc., Chem. Commun. 1970, 646
54. M. J S. Dewar, N. Trinajstic, J. Am. Chem. Soc. 1968, 90, 1953; M. J. S. Dewar, N. Trinajstic, J. Chem. Soc., Chem. Commun. 1970, 646
55. G. H. Posner, J. N. Cumming, P. Ploypradith, C. H. Ho, J. Am. Chem. Soc. 1995, 117, 5885.
56. H. R. Snyder, R. E. Heckert, J. Am. Chem. Soc. 1952, 74, 2006.
57. G H Posner, D. Wang, L. González, X. Tao, J. N. Cumming, D. Klinedinst, T. A. Shapiro, Tetrahedron Lett. 1996, 37, 815.
58. R. K. Haynes, S. C. Vonwiller, Tetrahedron Lett. 1996, 37, 253, 257.
59. W. Adam, B. Epe, D Schiffmann, F. Vargas, D. Wild, Angew, Chem. Int. Ed. 1988, 27, 429.
60. J. K Kochi, 'Free Radicals', Wiley-Interscience, New York, 1973, Vol. 1, Chapt. 11, Vol. 11, Chapt. 23; G. Sosnovsky, D. J. Rawlinson, in 'Organic Peroxides', Ed. S. Swern, Wiley-Interscience, New York, 1970, Vol. I; W Herz, R. C. Ligon, J. A. Turner, J. F. Blount, J. Org. Chem. 1977, 42, 1885; J. A. Turner, W. Herz, ibid. 1977, 42, 1900.
61. J. K Kochi, 'Free Radicals', Wiley-Interscience, New York, 1973, Vol. 1, Chapt. 11, Vol. 11, Chapt. 23; G. Sosnovsky, D. J. Rawlinson, in 'Organic Peroxides', Ed. S. Swern, Wiley-Interscience, New York, 1970, Vol. I; W Herz, R. C. Ligon, J. A. Turner, J. F. Blount, J. Org. Chem. 1977, 42, 1885; J. A. Turner, W. Herz, ibid. 1977, 42, 1900.
62. J. K Kochi, 'Free Radicals', Wiley-Interscience, New York, 1973, Vol. 1, Chapt. 11, Vol. 11, Chapt. 23; G. Sosnovsky, D. J. Rawlinson, in 'Organic Peroxides', Ed. S. Swern, Wiley-Interscience, New York, 1970, Vol. I; W Herz, R. C. Ligon, J. A. Turner, J. F. Blount, J. Org. Chem. 1977, 42, 1885; J. A. Turner, W. Herz, ibid. 1977, 42, 1900.
63. J. K Kochi, 'Free Radicals', Wiley-Interscience, New York, 1973, Vol. 1, Chapt. 11, Vol. 11, Chapt. 23; G. Sosnovsky, D. J. Rawlinson, in 'Organic Peroxides', Ed. S. Swern, Wiley-Interscience, New York, 1970, Vol. I; W Herz, R. C. Ligon, J. A. Turner, J. F. Blount, J. Org. Chem. 1977, 42, 1885; J. A. Turner, W. Herz, ibid. 1977, 42, 1900.
64. J. K Kochi, 'Free Radicals', Wiley-Interscience, New York, 1973, Vol. 1, Chapt. 11, Vol. 11, Chapt. 23; G. Sosnovsky, D. J. Rawlinson, in 'Organic Peroxides', Ed. S. Swern, Wiley-Interscience, New York, 1970, Vol. I; W Herz, R. C. Ligon, J. A. Turner, J. F. Blount, J. Org. Chem. 1977, 42, 1885; J. A. Turner, W. Herz, ibid. 1977, 42, 1900.
65. S. L. Schreiber, J. Am. Chem. Soc. 1980, 102, 6163.
66. W Asawamahasakda, I. Ittarat, C. Chang, P. McElroy, S. R Meshnick, Mol Biochem. Parasitol. 1994, 67, 183.
67. L Zhang, W. Zhou, X. Xu, J. Chem. Soc , Chem. Commun. 1988, 523.
68. C. W. Jefford, W. K. Milhous, unpublished; J. Vennerstrom, H. Fu, W, Y. Ellis, A. L. Ager, Jr., J. K. Wood, S. L. Anderson, L Gerena, W. K. Milhous, J. Med. Chem. 1992, 35, 3023.
69. C. W. Jefford, W. K. Milhous, unpublished; J. Vennerstrom, H. Fu, W, Y. Ellis, A. L. Ager, Jr., J. K. Wood, S. L. Anderson, L Gerena, W. K. Milhous, J. Med. Chem. 1992, 35, 3023.
70. J. Jakupovic, M. Grenz, G. Schmeda-Hirschmann, Phytochemistry 1988, 27, 2997.
71. T. V. Leibyuk, S. A. Shevtsov, V A. Raldugin, Khim. Prir. Soedin. 1990, 4, 556.