Fluoroartemisinins: Metabolically more stable antimalarial artemisinin derivatives

ChemMedChem

Volumn 2, Issue 5, 2007, Pages 608-624

  Bégué, Jean Pierre ^a   Bonnet Delpon, Danièle ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

Artemisinin; Drug metabolism; Fluorine; Malaria

Indexed keywords

ANTIMALARIAL AGENT; ARTEMISININ DERIVATIVE; ETHER DERIVATIVE; FLUORINE;

ANIMAL; CHEMISTRY; DRUG EFFECT; HALF LIFE TIME; MOUSE; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; RAT; REVIEW;

ANIMALS; ANTIMALARIALS; ARTEMISININS; ETHERS; FLUORINE; HALF-LIFE; MICE; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; RATS;

EID: 38949151540     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200600156     Document Type: Review

References (129)

1. a) J. G. Breman, Am. J. Trop. Med. Hyg. 2001, 64 (suppl.), 1-11;
2. b) N. J. White, F. Nosten, S. Looareesuwan, W. M. Watkins, K. Marsh, R. W. Snow, G. Kokwaro, J. Ouma, T. T. Hien, M. E. Molyneux, T. E. Taylor, C. I. Newbold, T. K. Ruebush II, M. Danis, B. M. Grennwood, R. M. Anderson, P. L. Olliaro, Lancet 1999, 353, 1965-1967.
3. P. L. Olliaro, P. B. Bloland in Antimalarial Chemotherapy: Mechanisms of Action, Resistance, and New Directions in Drug Discovery (Eds.: P. J. Rosenthal) Human, Totowa, NJ, 2001, pp. 65-83.
4. R. G. Ridley, Nature 2002, 415, 686-693.
5. R. C. Haynes, S. C. Vonwiller, Acc. Chem. Res. 1997, 30, 73-79.
6. P. O'Neill, G. H. Posner, J. Med. Chem. 2004, 47, 2945-2964.
7. N. X. Khanh, P. J. de Vries, L. Dang Ha, C. J. van Boxtel, R. Koopmans, P. A. Kager, Antimicrob. Agents Chemother. 1999, 43, 690-692.
8. a) Word Health Organization Antimalarial Drug Combinaison Therapy. Report of a WHO Technical Consultation. WHO/CDS/RBM/2001.35 Geneva, Switzerland: WHO;
9. b) P. E. Duffy, T. K. Mutabingwa, Lancet 2004, 363, 3-4.
10. M. A. Van Agtmael, T. A. Eggelte, C. J. van Boxtel, Trends Pharmacol. Sci. 1999, 20, 199-204.
11. a) K. F. Ilett, B.T Ethell, . J. L. Maggs, T. M. E. Davis, K.T Batty, B. Burchell, T. Quang Binh, L. T. Anh Thu, N. Canh Hung, M. Pirmohamed, B. K. Park, G. Edwards, Drug Metab. Dispos. 2002, 30, 1005-1012;
12. b) P. M. O'Neill, F. Scheinmann, A. V. Stachulski, J. L. Maggs, B. K. Park, J. Med. Chem. 2001, 44, 1467-1470.
13. J. P. Bégué, D. Bonnet-Delpon, Drugs Future 2005, 30, 509-522.
14. M. Jung, K. Lee, H. Kim, M. Park, Agents Curr. Med. Chem. 2004, 11, 1265-1284.
15. R. K. Haynes, H. W. Chan, M. K. Cheung, S. T. Chung, W. L. Lam, H. W. Tsang, A. Voerste, I. D. Williams, Eur. J. Org. Chem. 2003, 2098-2114.
16. R. K. Haynes, Curr. Opin. Infect. Dis. 2001, 14, 719-726.
17. Y. Li, Y. X. Chen, R. Y. Ji, Y. Z. Gai, D. S. Wang, Y. P. Zheng, Acta Pharm. Sin. 1981, 16, 557-561.
18. Y. M. Pu, H. Ziffer, J. Med. Chem. 1995, 38, 613-616.
19. J. Ma, E. Katz, D. E. Kyle, H. Ziffer, J. Med. Chem. 2000, 43, 4228-4232.
20. F. Chorki, F. Grellepois, M. Ourevitch, B. Crousse, D. Bonnet-Delpon, J. P. Bégué, J. Org. Chem. 2001, 66, 7858-7863.
21. R. K. Haynes, H.-W. Chan, M.-K. Cheung, W.-L. Lam, M.-K. Soo, H.-W. Tsang, A. Voerste, I. D. Williams, Eur. J. Org. Chem. 2002, 113-132.
22. G. H. Posner, M. H. Parker, J. Northrop, P. Ploypradith, S. Xie, T. A. Shapiro, J. Med. Chem. 1999, 42, 300-304.
23. S. H. Woo, N. P. Parker, P. Ploypradith, J. Northrop, G. H. Posner, Tetrahedron Lett. 1998, 39, 1533.
24. A. Abouabdellah, J. P. Bégué, D. Bonnet-Delpon, J. C. Gantier, T. T. Thanh Nga, T. Truong Dinh, Bioorg. Med. Chem. Lett. 1996, 6, 2717-2720.
25. V. D. Hoang, F. Chorki, F. Grellepois, B. Crousse, P. Grellier, T. T. Dien, D. Bonnet-Delpon, J. P. Bégué, Org. Lett. 2002, 4, 757-759.
26. P. M. O'Neill, A. Miller, L. P. D. Bisop, S. Hindley, J. L. Ward, S. M. Roberts, F. Scheimann, A. V. Stachulski, G. H. Posner, B. K. Park, J. Med. Chem. 2001, 44, 58-68.
27. Y. Ming Pu, D. S. Torok, H. Ziffer, J. Med. Chem. 1995, 38, 5045-5050.
28. R. K. Haynes, H. W. Chan, W. Y. Ho, C. K. F. Ko, L. Gerena, D. E. Kyle, W. Peters, B. L. Robinson, ChemBioChem 2005, 6, 659-667.
29. a) R. K. Haynes, Preparation of antiparasitic artemisinin derivatives PCT Int. Appl., WO 2003-EP1839 2003224, 2003 [Chem. Abstr. 139, 261439];
30. b) R. K. Haynes, B. Fugmann, J. Stetter, K. Rieckmann, H. D. Heilmann, Ho-Wai Chan, Man-Ki Cheung, Wai-Lun Lam, Ho-Ning Wong, S. L. Croft, L. Vivas, L. Rattray, L. Stewart, W. Peters, B. L. Robinson, M. D. Edstein, B. Kotecka, D. E. Kyle, B. Beckermann, M. Gerisch, M. Radtke, G. Schmuck, W. Steinke, U. Wollborn, K. Schmeer, A. Römer, Angew. Chem. 2006, 118, 2136-2142;
31. Angew. Chem. Int. Ed. 2006, 45, 2082-2088.
32. a) F. S. El-Feraly, A. Ayalp, M. A. Al-Yahya, D. R. McPhail, A. T. McPhail, J. Nat. Prod. 1990, 53, 66-71;
33. b) S. Paitayatat, B. Tarnchompoo, Y. Thebtaranonth, Y. Yuthavong, J. Med. Chem. 1997, 40, 633-638.
34. Y. Y. Ma, E. Weiss, D.E Kyle, H. Ziffer, Bioorg. Med. Chem. Lett. 2000, 10, 1601-1603.
35. M. A. Jung, K. Lee, H. Jung, Tetrahedron Lett. 2001, 42, 3997-4000.
36. R. K. Haynes, Curr. Top. Med. Chem. 2006, 6, 509-537.
37. S. Hindley, S. A. Ward, R. C. Storr, N. L. Searle, P. G. Bray, B. K. Park, J. Davies, P. M. O'Neill, J. Med. Chem. 2002, 45, 1052-1063.
38. a) J. P. Bégué, D. Bonnet-Delpon, Chimie Bioorganique et M dicinale du Fluor, EDP-Sciences/CNRS Editions, Paris, 2005, pp. 88-95;
39. b) J. P. Bégué, D. Bonnet-Delpon, Chimie Bioorganique et Médicinale du Fluor, EDP-Sciences/CNRS Editions, Paris, 2005, pp. 10-23;
40. c) J. P. Bégué, D. Bonnet-Delpon, Chimie Bioorganique et Médicinale du Fluor, EDP-Sciences/CNRS Editions, Paris, 2005, pp. 94>.
41. H. J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander, M. Stahl, ChemBioChem 2004, 5, 637-645.
42. B. E. Smart in Organofluorine Chemistry: Principles and Commercial Applications (Eds.: R. E. Bank, B. E. Smart, J. C. Tatlow), Plenum, New York, 1994, pp. 12.
43. Y. M. Pu, D. S. Torok, H. Ziffer, X. Q. Pan, S. R. Meshnick, J. Med. Chem. 1995, 38, 4120-4124.
44. The trifluoroethyl ether 9 a had been reported amongst a large number of ethers of DHA, with no details on preparation. A moderate in vivo activity was claimed, China Cooperative Research Group Trad. Chin. Med. 1982, 2, 9-14.
45. a) I. S. Lee, C. D. Hufford, Pharmacol. Ther. 1990, 48, 345-355;
46. b) V. Leskovac, A. D. Theoharides, Comp. Biochem. Physiol. Part C 1991, 99, 383-390;
47. c) V. Leskovac, A. D. Theoharides, Comp. Biochem. Physiol. Part C 1991, 99, 391-396.
48. a) J. Legros, B. Crousse, M. Maruta, D. Bonnet-Delpon, J. P. Bégué, Tetrahedron 2002, 58, 4067-4070;
49. b) J. Irrupe, J. Casas, A. Messeguer, Bioorg. Med. Chem. Lett. 1993, 3, 179-182.
50. a) T. G. C. Bird, P. M. Fredericks, E. R. H. Jones, G. D. Meakins, J. Chem. Soc. Perkin Trans. 1 1980, 750-755;
51. b) G. Haufe, D. Wölker, Eur. J. Org. Chem. 2003, 2159-2175.
52. a) A. J. Lin, M. Lee, D. L. Klayman, J. Med. Chem. 1989, 32, 1249-1252;
53. b) A. J. Lin, D. L. Klayman, W. K. Milhous, J. Med. Chem. 1987, 30, 2147-2150;
54. c) A. J. Lin, L. Q. Li, S. L. Andersen, D. L. Klayman, J. Med. Chem. 1992, 35, 1639-1642;
55. d) A. J. Lin, R. E. Miller, J. Med. Chem. 1995, 38, 764-770.
56. T. T. Thanh Nga, C. Ménage, J. P. Bégué, D. Bonnet-Delpon, J. C. Gantier, B. Pradines, J. C. Doury, T. D. Truong, J. Med. Chem. 1998, 41, 4101-4108.
57. The stereochemistry of C-10 substituted artemisinins is usually designated using the "steroid" convention (a below the molecule plan, β above) and not the convention used in carbohydrate series.
58. a) V. D. Hoang, P. G. Dien, N. V. Hung, J. P. Bégué, D. Bonnet-Delpon, Tap Chi Hoa Hoc 2003, 41, 17-18;
59. b) T. Van Nhu, D. Hanh Nhan, N. T. Minh Thu, J.-P. Bégué, D. Bonnet-Delpon, N. Van Hung, V. Dinh Hoang, Rev. Pharm. 2005, 1, 12-16.
60. a) J. R. Falck, J. Yu, H. S. Cho, Tetrahedron Lett. 1994, 35, 5997-6000;
61. b) H. S. Cho, J. Yu, J. R. Falck, J. Am. Chem. Soc. 1994, 116, 8354-8355;
62. c) D. P. Sebesta, S. S. O'Rourke, W. A. Pieken, J. Org. Chem. 1996, 61, 361-362.
63. a) A. L. Henne, W. C. Francis, J. Am. Chem. Soc. 1953, 75, 991-992;
64. b) J. P. Bégué, D. Bonnet-Delpon, B. Crousse, Synlett 2004, 18-24.
65. a) M. L. Sinnott, W. P. Jencks, J. Am. Chem. Soc. 1980, 102, 2026-2032;
66. b) A. Vasella, K. Briner, N. Soundararajan, M. S. Platz, J. Org. Chem. 1991, 56, 4741-4744;
67. c) K. Briner, A. Vasella, Helv. Chim. Acta 1992, 75, 621-635;
68. d) H. Maeda, S. Matsumoto, T. Koide, H. Ohmori, Chem. Pharm. Bull. 1998, 46, 939-943.
69. D. Gueyrard, P. Rollin, T. T. Thanh Nga, M. Ourévitch, J. P. Bégué, D. Bonnet-Delpon, Carbohydr. Res. 1999, 318, 171-179.
70. -1), K. A. McIntosh, W. N. Charman et al., unpublished results.
71. F. Grellepois, F. Chorki, B. Crousse, M. Ourévitch, D. Bonnet-Delpon, J. P. Bégué, J. Org. Chem. 2002, 67, 1253-1260.
72. a) G. Bott, L. D. Field, S. Sternhell, J. Am. Chem. Soc. 1980, 102, 5618-5626;
73. b) T. Nagai, G. Nishioka, M. Koyama, A. Ando, T. Miki, I. Kumadaki, Chem. Pharm. Bull. 1991, 39, 233-235.
74. G. Magueur, B. Crousse, D. Bonnet-Delpon, J. P. Bégué, J. Org. Chem. 2003, 68, 9763-9766.
75. a) A. D. Allen, T. T. Tidwell in Advances in Carbocation Chemistry; (Ed.: X. Creary), JAI, Greenwich, CT, 1989; pp. 1-44;
76. b) X. Creary, Chem. Rev. 1991, 91, 1625-1676;
77. c) A. Chennoufi, B. Malézieux, M. Gruselle, D. Bonnet-Delpon, J. P. Bégué, Org. Lett. 2000, 2, 807-809.
78. C. Reichadt, Solvents and solvent effects in organic chemistry, 3rd ed., Wiley-VCH, Weinheim, 2003.
79. B. Allard, A. Casadevall, E. Casadevall, C. Largeau, Nouv. J. Chim. 1980, 4, 539-545.
80. L. Eberson, M. P. Hartshorn, O. Persson, F. Radner, Chem. Commun. 1996, 2105-2112.
81. see for instance: a) J. Ichikawa, S. Miyazaki, M. Fujiwara, T. Minami, J. Org. Chem. 1995, 60, 2320-2232;
82. b) R. Takita, T. Oshima, M. Shibasaki, Tetrahedron Lett. 2002, 43, 4661-4665;
83. c) M. S. Cooper, H. Heaney, A. J. Newbold, W. R. Sanderson, Synlett 1990, 533-535;
84. d) J. Legros, B. Crousse, D. Bonnet-Delpon, J. P. Bégué, Eur. J. Org. Chem. 2002, 3290-3293;
85. e) U. Das, B. Crousse, V. Kesavan, D. Bonnet-Delpon, J. P. Bégué, J. Org. Chem. 2000, 65, 6749-6751.
86. a) A. Di Salvo, M. David, B. Crousse, D. Bonnet-Delpon, Adv. Synth. Catal. 2006, 118-124;
87. b) D. Bonnet-Delpon, B. Crousse, J. F. Berrien, unpublished.
88. S. A.-L. Laurent, A. Robert, B. Meunier, Angew. Chem. 2005, 117,2096-2099;
89. Angew. Chem. Int. Ed. 2005, 44, 2060-2063.
90. J. P. Bégué, F. Benayoud, D. Bonnet-Delpon, J. Org. Chem. 1995, 60, 5029-5036.
91. G. Magueur, B. Crousse, S. Charneau, P. Grellier, J. P. Bégué, D. Bonnet-Delpon, J. Med. Chem. 2004, 47, 2694-2699.
92. F. Grellepois, F. Chorki, M. Ourévitch, S. Charneau, P. Grellier, K. A. McIntosh, W. N. Charman, B. Pradines, B. Crousse, D. Bonnet-Delpon, J. P. Bégué, J. Med. Chem. 2004, 47, 1423-1433.
93. a) P. D. Binh, Le Dinh Cong, D. H. Nhan, T. V. Nhu, N. T. Tien, J. P. Bégué, D. Bonnet-Delpon, T. T. Thanh Nga, Trans. R. Soc. Trop. Med. Hyg. 2002, 96, 677-683;
94. b) T. V. Nhu, D. H. Nhan, N. T. Minh Thu, J. P. Bégué, D. Bonnet-Delpon, N. V. Hung, V. D. Hoang, Rev. Pharm. 2005, 1, 12-16.
95. W. G. McLean, et al. unpublished results.
96. T. V.Nhu, D. H., Nhan, N. T. M. Thu et al., unpublished results.
97. a) N. O. Brace, J. Fluorine Chem. 1995, 93, 1-25;
98. b) G. G. Furin, Russ. Chem. Rev. 2000, 69, 491-522.
99. M. Jung, X. Li, D. A. Bustos, H. N. El Sohly, J. D. McChesney, W. K. Milhous, J. Med. Chem. 1990, 33, 1516.
100. D. H. R. Barton, S. W. McCombie, J. Chem. Soc. Perkin Trans. 1 1975, 1574.
101. P. Boussaguet, B. Delmond, G. Dumartin, M. Pereyre, Tetrahedron Lett. 2000, 41, 3377-3380.
102. B. Venugopalan, P. J. Karnik, C. P. Bapat, D. K. Chatterjee, N. Iyer, D. Lepcha, Eur. J. Med. Chem. 1995, 30, 697-706.
103. T. F. Herpin, W. B. Motherwell, S. Roland, J. M. Weibel, Tetrahedron 1997, 53, 15083-15100, and references therein.
104. D. J. Burton, Z. Y. Yang, Chem. Rev. 1996, 96, 1641-1716.
105. J. S. Houlton, W. B. Motherwell, B. C. Ross, M. J. Tozer, D. J. Williams, A. M. Z. Slawin, Tetrahedron 1993, 49, 8087-8106.
106. G. Magueur, B. Crousse, M. Ourévitch, D. Bonnet-Delpon, J. P. Bégué, J. Fluorine Chem. 2006, 127, 637-642.
107. H. Berber, T. Brigaud, O. Lefebvre, R. Plantier-Royon, C. Portella, Chem. Eur. J. 2001, 7, 903-909.
108. H. Amii, T. Kobayashi, Y. Hatamoto, K. Uneyama, Chem. Commun. 1999, 1323-1324.
109. F. Chorki, B. Crousse, T. Brigaud, D. Bonnet-Delpon, C. Portella, J. P. Bégué, Tetrahedron Lett. 2001, 42, 1487-1490.
110. D. Y. Wang, Y. L. Wu, Y. Wu, Y. Li, J. Chem. Soc. Perkin Trans. 1 2001, 605-609.
111. Y.-M. Pu, H. J. C. Yeh, H. Ziffer, Heterocycles 1993, 36, 2099-2107.
112. C. W. Jefford, J. C. Rossier, J. Boukouvalas, J. Chem. Soc. Chem. Commun. 1987, 713-714.
113. F. Grellepois, D. Bonnet-Delpon, J. P. Bégué, Tetrahedron Lett. 2001, 42, 2125-2127.
114. A. J. Lin, L. Li, D. L. Klayman, C. F. George, J. L. T. Flippen-Anderson, J. Med. Chem. 1990, 33, 2610-2614.
115. X. Creary, Chem. Rev. 1991, 91, 1625-1678.
116. B. Venugopalan, C. P. Bapat, P. J. Karnik, B. Lal, D. K. Chatterjee, S. N. Iyer, J. Blumbach, Eur. Pat. EP. 456, 149, 1991 [Chem. Abstr. 1992, 116, 83708z].
117. B. Venugopalan, C. P. Bapat, P. J. Karnik, Bioorg. Med. Chem. Lett. 1994, 4, 750-752.
118. B. Venugopalan, C. P. Bapat, P. J. Karnik, B. Lal, D. K. Chatterjee, S. N. Iyer, D. Lepcha, J. Med. Chem. 1995, 38, 1922-1927.
119. S. Ekthawatchai, S. Kamchonwongpaisan, P. Kongsaeree, B. Tarnchompoo, Y. Thebtaranonth, Y. Yuthav ong, J. Med. Chem. 2001, 44, 4688-4695.
120. X. B. Liao, J. Y. Han, Y. Li, Tetrahedron Lett. 2000, 41, 2843-2845.
121. a) M. Jung, D. A. Bustos, H. N. El Sohly, J. D. McChesney, Synlett 1990, 743-744;
122. b) M. Jung, D. A. Bustos, H. N. El Sohly, J. D. McChesney. Bioorg. Med. Chem. Lett. 1991, 1, 741-744;
123. c) R. K. Haynes, S. C. Vonwiller. Synlett 1992, 481-483.
124. C. Djerassi, Chem. Rev. 1948, 48, 271-317.
125. F. Grellepois, F. Chorki, M. Ourévitch, B. Crousse, D. Bonnet-Delpon, J. P. Bégué, Tetrahedron Lett. 2002, 43, 7837-7840.
126. D. Bonnet-Delpon, D. Bouvet, M. Ourévitch, M. Rock, Synthesis 1998, 288-292.
127. E. F. V. Scriven, K. Turnbull, Chem. Rev. 1988, 88, 297-368.
128. Y. M. Pu, B. Yagen, H. Ziffer, Tetrahedron Lett. 1994, 35, 2129-2132.
129. C. Chollet, B. Crousse, M. Ourévitch, D. Bonnet-Delpon, J. Org. Chem. 2006, 71, 3082-3083.