Synthesis and in vivo antimalarial activity of 12α-trifluoromethyl-hydroartemisinin

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 22, 1996, Pages 2717-2720

  Abouabdellah, Ahmed ^a   Bégué, Jean Pierre ^a   Bonnet Delpon, Danièle ^a   Gantier, Jean Charles ^b   Nga, Truong Thi Thanh ^a   Thac, Truong Dinh ^c  

^a UNIVERSITÉ PARIS SUD   (France)

^b Centre d'Etudes Pharmaceutiques   (France)

^c Institut de Chimie Industrielle   (Viet Nam)

Author keywords

[No Author keywords available]

Indexed keywords

12ALPHA TRIFLUOROMETHYLHYDROARTEMISININ; ANTIMALARIAL AGENT; ARTEMISININ; ARTEMISININ DERIVATIVE; CHLOROQUINE; UNCLASSIFIED DRUG;

ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; MALARIA; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; ORAL DRUG ADMINISTRATION; PLASMODIUM VINCKEI; STEREOCHEMISTRY;

ANIMALIA; PLASMODIUM VINCKEI;

EID: 0010646449     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00488-X     Document Type: Article

References (35)

1. 1. China Cooperative Research Group on Qinghaosu and its Derivatives as Antimalarials Chinese Medical Journal 1979, 92, 811-818 (Engl. edit.).
2. 2. Luo, X.D.; Shen, C.C. Med. Res. Rev. 1987, 7, 29-52.
3. 3. (a) Jung, M. Curr. Med. Chem. 1994, 1, 35-49.
4. (b) Venugopalan, B.; Karnik, P.J.; Bapat, C.P.; Lyer, N.; Lepcha, D. Eur. J. Med. Chem. 1995, 30, 697-706.
5. (c) Ramu, K.; Baker, J.K. J. Med. Chem. 1995, 38, 1911-1921.;
6. (d) Brossi, A.; Venugopalan, B.; Gerpe, L.D.; Yeh, H.J.C.; Flippen-Anderson, J.L.; Buchs, P.; Luo, X.D.; Milhous, W.K.; Peters, W. J. Med. Chem. 1988, 31, 645-650.
7. (e) Lin, A.J.; Klayman, D.L.; Milhous, W.K. J. Med. Chem. 1987, 30, 2147-2150.
8. (f) Lin, A.J.; Miller, R.E. J. Med. Chem. 1995, 38, 764-770.
9. 4. Chi, H.T.; Ramu, K.; Baker, J.K.; Hufford, C.D.; Lee, I.S.; Zeng, Y.L.; Mc Chesney, D. J. Biol. Mass Spectrom. 1991, 609-628.
10. 5. Leskovac, V.; Theoharides, A.D. Comp. Biochem. Physiol. 1991, 99, 383-390. Leskovac, V.; Theoharides, A.D. Comp. Biochem. Physiol. 1991, 99, 391-396.
11. 5. Leskovac, V.; Theoharides, A.D. Comp. Biochem. Physiol. 1991, 99, 383-390. Leskovac, V.; Theoharides, A.D. Comp. Biochem. Physiol. 1991, 99, 391-396.
12. 6. Park, B.K.; Kitteringham, N.R., Drug Metabolism Rev. 1994, 26, 605-643. Irurre, J.; Casas, J.; Messeguer, A., Biorg. Med. Chem. Lett. 1993, 3, 179-182. Miller, J.A.; Coleman, M.C.; Matthews, R.S. J. Org. Chem. 1993, 58, 2637-2639. O'Neill, P.M.; Harrison, A.C.; Storr, R.C.; Ward, S.A.; Park, B.K. J. Med. Chem. 1994, 37, 1362-1370. Diana, G.D.; Rudewicz, P.; Pevear, D.C.; Nitz, T.J.; Aldous, S.C.; Aldous, D.J.; Robinson, D.T.; Draper, T.; Dutko, F.J.; Aldi, C.; Gendron, G.; Oglesby, R.C.; Volkots, D.L.; Reuman, M.; Bailey, T.R.; Czerniak, R.; Block, T.; Roland, R.; Oppermann, J. J. Med. Chem. 1995, 38, 1355-1371.
13. 6. sdPark, B.K.; Kitteringham, N.R., Drug Metabolism Rev. 1994, 26, 605-643. Irurre, J.; Casas, J.; Messeguer, A., Biorg. Med. Chem. Lett. 1993, 3, 179-182. Miller, J.A.; Coleman, M.C.; Matthews, R.S. J. Org. Chem. 1993, 58, 2637-2639. O'Neill, P.M.; Harrison, A.C.; Storr, R.C.; Ward, S.A.; Park, B.K. J. Med. Chem. 1994, 37, 1362-1370. Diana, G.D.; Rudewicz, P.; Pevear, D.C.; Nitz, T.J.; Aldous, S.C.; Aldous, D.J.; Robinson, D.T.; Draper, T.; Dutko, F.J.; Aldi, C.; Gendron, G.; Oglesby, R.C.; Volkots, D.L.; Reuman, M.; Bailey, T.R.; Czerniak, R.; Block, T.; Roland, R.; Oppermann, J. J. Med. Chem. 1995, 38, 1355-1371.
14. 6. Park, B.K.; Kitteringham, N.R., Drug Metabolism Rev. 1994, 26, 605-643. Irurre, J.; Casas, J.; Messeguer, A., Biorg. Med. Chem. Lett. 1993, 3, 179-182. Miller, J.A.; Coleman, M.C.; Matthews, R.S. J. Org. Chem. 1993, 58, 2637-2639. O'Neill, P.M.; Harrison, A.C.; Storr, R.C.; Ward, S.A.; Park, B.K. J. Med. Chem. 1994, 37, 1362-1370. Diana, G.D.; Rudewicz, P.; Pevear, D.C.; Nitz, T.J.; Aldous, S.C.; Aldous, D.J.; Robinson, D.T.; Draper, T.; Dutko, F.J.; Aldi, C.; Gendron, G.; Oglesby, R.C.; Volkots, D.L.; Reuman, M.; Bailey, T.R.; Czerniak, R.; Block, T.; Roland, R.; Oppermann, J. J. Med. Chem. 1995, 38, 1355-1371.
15. 6. Park, B.K.; Kitteringham, N.R., Drug Metabolism Rev. 1994, 26, 605-643. Irurre, J.; Casas, J.; Messeguer, A., Biorg. Med. Chem. Lett. 1993, 3, 179-182. Miller, J.A.; Coleman, M.C.; Matthews, R.S. J. Org. Chem. 1993, 58, 2637-2639. O'Neill, P.M.; Harrison, A.C.; Storr, R.C.; Ward, S.A.; Park, B.K. J. Med. Chem. 1994, 37, 1362-1370. Diana, G.D.; Rudewicz, P.; Pevear, D.C.; Nitz, T.J.; Aldous, S.C.; Aldous, D.J.; Robinson, D.T.; Draper, T.; Dutko, F.J.; Aldi, C.; Gendron, G.; Oglesby, R.C.; Volkots, D.L.; Reuman, M.; Bailey, T.R.; Czerniak, R.; Block, T.; Roland, R.; Oppermann, J. J. Med. Chem. 1995, 38, 1355-1371.
16. 6. Park, B.K.; Kitteringham, N.R., Drug Metabolism Rev. 1994, 26, 605-643. Irurre, J.; Casas, J.; Messeguer, A., Biorg. Med. Chem. Lett. 1993, 3, 179-182. Miller, J.A.; Coleman, M.C.; Matthews, R.S. J. Org. Chem. 1993, 58, 2637-2639. O'Neill, P.M.; Harrison, A.C.; Storr, R.C.; Ward, S.A.; Park, B.K. J. Med. Chem. 1994, 37, 1362-1370. Diana, G.D.; Rudewicz, P.; Pevear, D.C.; Nitz, T.J.; Aldous, S.C.; Aldous, D.J.; Robinson, D.T.; Draper, T.; Dutko, F.J.; Aldi, C.; Gendron, G.; Oglesby, R.C.; Volkots, D.L.; Reuman, M.; Bailey, T.R.; Czerniak, R.; Block, T.; Roland, R.; Oppermann, J. J. Med. Chem. 1995, 38, 1355-1371.
17. 7. China Cooperative Res. Group on Qinghaosu and its Derivatives as Antimalarials. J. Tradit. Chin. Med. 1982, 2, 9-16.
18. 8. Pu, Y.M.; Torok, D.S.; Ziffer, H.; Pan, X.Q.; Meshnick, J.R. J. Med. Chem. 1995, 38, 4120-4124.
19. 9. Haynes, R.K.; Vonwiller, S. Synlett 1992, 481-484.
20. 10. Pu, Y.M.; Ziffer, H. J. Med. Chem. 1995, 38, 613-616;
21. 11. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 25, 2195-2198.
22. 12. Krishnamurti, R.; Olah, G.A.; Prakash, G.K.S. J. Am. Chem. Soc. 1989, 111, 393-395.
23. 13. Skiles, J.W.; Fuchs, V.; Miao, C.; Sorcek, R.; Grozinger, K.G.; Mauldin, S.C.; Vitous, J.; Mui, P.W.; Jacober, S.; Chow, G.; Matteo, M.; Skoog, M.; Weldon, S.M.; Possanza, G.; Keirns, J.; Letts, G.; Rosenthal, A.S. J. Med. Chem. 1992, 35, 641-662; Combs, M.M.; Zepik, H.H. J. Chem. Soc. Chem. Comm. 1992, 1376-1377; Wang, Z.; Ruan, B. J. Fluorine chem. 1994, 69, 1-3; Kozikowski, A.P.; Roberti, M.; Johnson, K.M.; Bergmann, J.S.; Ball, R.B. Bioorg. Med. Chem. Lett. 1993, 3, 1327-1332; Wang, Z.Q.; Lu, S.F.; Chao, L.; Yang, C.J. Bioorg. Med. Chem. Lett. 1995, 5, 1899-1902; Bansai, R.C.; Dean, B.; Hakomori, S.; Toyokuni, T. J. Chem. Soc. Chem. Comm. 1991, 796-798.
24. 13. Skiles, J.W.; Fuchs, V.; Miao, C.; Sorcek, R.; Grozinger, K.G.; Mauldin, S.C.; Vitous, J.; Mui, P.W.; Jacober, S.; Chow, G.; Matteo, M.; Skoog, M.; Weldon, S.M.; Possanza, G.; Keirns, J.; Letts, G.; Rosenthal, A.S. J. Med. Chem. 1992, 35, 641-662; Combs, M.M.; Zepik, H.H. J. Chem. Soc. Chem. Comm. 1992, 1376-1377; Wang, Z.; Ruan, B. J. Fluorine chem. 1994, 69, 1-3; Kozikowski, A.P.; Roberti, M.; Johnson, K.M.; Bergmann, J.S.; Ball, R.B. Bioorg. Med. Chem. Lett. 1993, 3, 1327-1332; Wang, Z.Q.; Lu, S.F.; Chao, L.; Yang, C.J. Bioorg. Med. Chem. Lett. 1995, 5, 1899-1902; Bansai, R.C.; Dean, B.; Hakomori, S.; Toyokuni, T. J. Chem. Soc. Chem. Comm. 1991, 796-798.
25. 13. Skiles, J.W.; Fuchs, V.; Miao, C.; Sorcek, R.; Grozinger, K.G.; Mauldin, S.C.; Vitous, J.; Mui, P.W.; Jacober, S.; Chow, G.; Matteo, M.; Skoog, M.; Weldon, S.M.; Possanza, G.; Keirns, J.; Letts, G.; Rosenthal, A.S. J. Med. Chem. 1992, 35, 641-662; Combs, M.M.; Zepik, H.H. J. Chem. Soc. Chem. Comm. 1992, 1376-1377; Wang, Z.; Ruan, B. J. Fluorine chem. 1994, 69, 1-3; Kozikowski, A.P.; Roberti, M.; Johnson, K.M.; Bergmann, J.S.; Ball, R.B. Bioorg. Med. Chem. Lett. 1993, 3, 1327-1332; Wang, Z.Q.; Lu, S.F.; Chao, L.; Yang, C.J. Bioorg. Med. Chem. Lett. 1995, 5, 1899-1902; Bansai, R.C.; Dean, B.; Hakomori, S.; Toyokuni, T. J. Chem. Soc. Chem. Comm. 1991, 796-798.
26. 13. Skiles, J.W.; Fuchs, V.; Miao, C.; Sorcek, R.; Grozinger, K.G.; Mauldin, S.C.; Vitous, J.; Mui, P.W.; Jacober, S.; Chow, G.; Matteo, M.; Skoog, M.; Weldon, S.M.; Possanza, G.; Keirns, J.; Letts, G.; Rosenthal, A.S. J. Med. Chem. 1992, 35, 641-662; Combs, M.M.; Zepik, H.H. J. Chem. Soc. Chem. Comm. 1992, 1376-1377; Wang, Z.; Ruan, B. J. Fluorine chem. 1994, 69, 1-3; Kozikowski, A.P.; Roberti, M.; Johnson, K.M.; Bergmann, J.S.; Ball, R.B. Bioorg. Med. Chem. Lett. 1993, 3, 1327-1332; Wang, Z.Q.; Lu, S.F.; Chao, L.; Yang, C.J. Bioorg. Med. Chem. Lett. 1995, 5, 1899-1902; Bansai, R.C.; Dean, B.; Hakomori, S.; Toyokuni, T. J. Chem. Soc. Chem. Comm. 1991, 796-798.
27. 13. Skiles, J.W.; Fuchs, V.; Miao, C.; Sorcek, R.; Grozinger, K.G.; Mauldin, S.C.; Vitous, J.; Mui, P.W.; Jacober, S.; Chow, G.; Matteo, M.; Skoog, M.; Weldon, S.M.; Possanza, G.; Keirns, J.; Letts, G.; Rosenthal, A.S. J. Med. Chem. 1992, 35, 641-662; Combs, M.M.; Zepik, H.H. J. Chem. Soc. Chem. Comm. 1992, 1376-1377; Wang, Z.; Ruan, B. J. Fluorine chem. 1994, 69, 1-3; Kozikowski, A.P.; Roberti, M.; Johnson, K.M.; Bergmann, J.S.; Ball, R.B. Bioorg. Med. Chem. Lett. 1993, 3, 1327-1332; Wang, Z.Q.; Lu, S.F.; Chao, L.; Yang, C.J. Bioorg. Med. Chem. Lett. 1995, 5, 1899-1902; Bansai, R.C.; Dean, B.; Hakomori, S.; Toyokuni, T. J. Chem. Soc. Chem. Comm. 1991, 796-798.
28. 13. Skiles, J.W.; Fuchs, V.; Miao, C.; Sorcek, R.; Grozinger, K.G.; Mauldin, S.C.; Vitous, J.; Mui, P.W.; Jacober, S.; Chow, G.; Matteo, M.; Skoog, M.; Weldon, S.M.; Possanza, G.; Keirns, J.; Letts, G.; Rosenthal, A.S. J. Med. Chem. 1992, 35, 641-662; Combs, M.M.; Zepik, H.H. J. Chem. Soc. Chem. Comm. 1992, 1376-1377; Wang, Z.; Ruan, B. J. Fluorine chem. 1994, 69, 1-3; Kozikowski, A.P.; Roberti, M.; Johnson, K.M.; Bergmann, J.S.; Ball, R.B. Bioorg. Med. Chem. Lett. 1993, 3, 1327-1332; Wang, Z.Q.; Lu, S.F.; Chao, L.; Yang, C.J. Bioorg. Med. Chem. Lett. 1995, 5, 1899-1902; Bansai, R.C.; Dean, B.; Hakomori, S.; Toyokuni, T. J. Chem. Soc. Chem. Comm. 1991, 796-798.
29. 14. Krishnamurti, R.; Bellew, D.R.; Prakash, G.K.S. J. Org. Chem. 1991, 56, 984-989.
30. 5: C, 54.54 %, H, 6.58; Found: C, 54.55 %; H, 6.59.
31. 6 red cells parasited by strain 279 BY (Prof. Landau, Museum National Histoire Naturelle, Paris). Each group contained ten mice.
32. 17. Caillard, V.; Beauté-Lafitte, A.; Chabaud, A.G.; Landau, I. Exp. Parasitol. 1992, 75, 449-456. Montalvo-Alvarez, A.M.; Landau, I.; Baccam, D.; Chabaud, A.G.; Ginsburg, H. C. R. Acad. Sci. Paris, 1988, 307, (serie III) 5-10.
33. 17. Caillard, V.; Beauté-Lafitte, A.; Chabaud, A.G.; Landau, I. Exp. Parasitol. 1992, 75, 449-456. Montalvo-Alvarez, A.M.; Landau, I.; Baccam, D.; Chabaud, A.G.; Ginsburg, H. C. R. Acad. Sci. Paris, 1988, 307, (serie III) 5-10.
34. -1 concentration as a suspension, in an aqueous solution of carboxymethyl cellulose (1 %). The control group received only carboxymethyl cellulose excipient at 0.1 %.
35. 19. Cambie, G.; Caillard, V.; Beauté-Lafitte, A.; Ginsburg, H.; Chabaud, A.G.; Landau, I. Ann. Parasitol. Hum. Comp. 1991, 66, 14-21.