Design and synthesis of endoperoxide antimalarial prodrug models

Angewandte Chemie - International Edition

Volumn 43, Issue 32, 2004, Pages 4193-4197

  O'Neill, Paul M ^a   Stocks, Paul A ^a   Pugh, Matthew D ^a   Araujo, Nuna C ^a   Korshin, Edward E ^b   Bickley, Jamie F ^a   Ward, Stephen A ^c   Bray, Patrick G ^c   Pasini, Erica ^c   Davies, Jill ^a   Verissimo, Edite ^a   Bachi, Mario D ^b  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^c LIVERPOOL SCHOOL OF TROPICAL MEDICINE   (United Kingdom)

Author keywords

Antimalarial agents; Chalcones; Combination chemotherapy; Cysteine protease inhibitors; Endoperoxides

Indexed keywords

CHEMOTHERAPY; MALARIA CONTROL; MATHEMATICAL MODELS; PEROXIDES; SYNTHESIS (CHEMICAL);

ANTIMALARIAL PRODRUG MODELS; CHEMICAL ENTITY;

DRUG PRODUCTS;

ANTIMALARIAL AGENT; ARTEFLENE; ARTEMISININ; ENDOPEROXIDE; PRODRUG;

ARTICLE; CHEMICAL REACTION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; FRAGMENTATION REACTION; MOLECULAR MODEL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

ANTIMALARIALS; BICYCLO COMPOUNDS; CHALCONES; CYSTEINE PROTEINASE INHIBITORS; DRUG DESIGN; PEROXIDES; PRODRUGS;

EID: 4544263432     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200453859     Document Type: Article

References (64)

1. P. J. Guerin, P. Olliaro, F. Nosten, P. Druilhe, R. Laxminarayan, F. Binka, W. L. Kilama, N. Ford, N. J. White, Lancet Infect. Dis. 2002, 2, 564-573.
2. M. Frederich, J. M. Dogne, L. Angenot, P. De Mol, Curr. Med. Chem. 2002, 9, 1435-1456.
3. S. Pukrittayakamee, N. J. White, Pharm. News 2001, 8, 21-26.
4. a) A. Robert, O. Dechy-Cabaret, J. Cazelles, B. Meunier, Acc. Chem. Res. 2002, 35, 167-174;
5. b) O. Dechy-Cabaret, F. Benoit-Vical, A. Robert, B. Meunier, ChemBioChem 2000, 1, 281-283;
6. c) L. K. Basco, O. Dechy-Cabaret, M. Ndounga, F. S. Meche, A. Robert, B. Meunier, Antimicrob. Agents Chemother. 2001, 45, 1886-1888.
7. O. Dechy-Cabaret, A. Robert, B. Meunier, C. R. Chim. 2002, 5, 297-302.
8. 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.
9. a) G. H. Posner, S. B. Park, L. Gonzalez, D. Wang, J. N. Cumming, D. Klinedinst, T. A. Shapiro, M. D. Bachi, J. Am. Chem. Soc. 1996, 118, 3537-3538;
10. b) J. N. Cumming, P. Ploypradith, G. H. Posner, Adv. Pharmacol. 1997, 37, 253-297;
11. c) G. H. Posner, J. N. Cumming, M. Krasavin in Biomedicinal Chemistry: Applying Chemical Principles to the Understanding and Treatment of Disease (Ed.: P. F. Torrence), Wiley-Interscience, New York, 2000, pp. 289-309;
12. d) K. Borstnik, I.-H. Paik, G.H. Posner, Mini-Rev. Med. Chem. 2002, 2, 573-583.
13. a) A. Robert, J. Cazelles, B. Meunier, Angew. Chem. 2001, 113, 2008-2011; Angew. Chem. Int. Ed. 2001, 40, 1954-1957;
14. a) A. Robert, J. Cazelles, B. Meunier, Angew. Chem. 2001, 113, 2008-2011; Angew. Chem. Int. Ed. 2001, 40, 1954-1957;
15. b) A. Robert, B. Meunier, J. Am. Chem. Soc. 1997, 119, 5968-5969;
16. c) Y. Wu, Acc. Chem. Res. 2002, 35, 255-259;
17. d) Y. Wu, Z.-Y. Yue, Y.-L. Wu, Angew. Chem. 1999, 111, 2730-2733; Angew. Chem. Int. Ed. 1999, 38, 2580-2583;
18. d) Y. Wu, Z.-Y. Yue, Y.-L. Wu, Angew. Chem. 1999, 111, 2730-2733; Angew. Chem. Int. Ed. 1999, 38, 2580-2583;
19. e) C. W. Jefford, Curr. Med. Chem. 2001, 8, 1803-1826.
20. a) S. R. Meshnick, T. E. Taylor, S. Kamchonwongpaisan, Microbiol. Rev. 1996, 60, 301-315;
21. b) S. R. Meshnick, Int. J. Parasitol. 2002, 32, 1655-1660;
22. c) Y.-L. Hong, Y.-Z. Yang, S. R. Meshnick, Mol. Biochem. Parasitol. 1994, 63, 121-128;
23. d) W. Asawamahasakda, I. Ittarat, Y.-M. Pu, H. Ziffer, S. R. Meshnick, Antimicrob. Agents Chemother. 1994, 38, 1854-1858;
24. e) J. Bhisutthibhan, X.-Q. Pan, P. A. Hossler, D. J. Walker, C. A. Yowell, J. Carlton, J. B. Dame, S. R. Meshnick, J. Biol. Chem. 1998, 273, 16192-16198;
25. f) A. V. Pandey, B. L. Tekwani, R. L. Singh, V. S. Chauhan, J. Biol. Chem. 1999, 274, 19383-19388;
26. g) U. Eckstein-Ludwig, R. J. Webb, I. D. A. van Goethem, J. M. East, A. G. Lee, M. Kimura, P. M. O'Neill, P. G. Bray, S. A. Ward, S. Krishna, Nature 2003, 424, 957-961.
27. R. Li, G. L. Kenyon, F. E. Cohen, X. Chen, B. Gong, J. N. Dominguez, E. Davidson, G. Kurzban, R. E. Miller, E. O. Nuzum, P. J. Rosenthal, J. H. McKerrow, J. Med. Chem. 1995, 38, 5031-5037.
28. a) M. Chen, T. G. Theander, S. B. Christensen, L. Hviid, L. Zhai, A. Kharazmi, Antimicrob. Agents Chemother. 1994, 38, 1470-1475;
29. b) L. Nadelmann, J. Tjornelund, S. H. Hanse, C. Cornetti, U. G. Sidelmann, Xenobiotica 1997, 27, 667-680.
30. a) P. J. Rosenthal, Emerging Infect. Dis. 1998, 4, 49-57;
31. b) P. J. Rosenthal, Adv. Parasitol. 1999, 43, 105-159;
32. c) P. J. Rosenthal, J. H. McKerrow, M. Aikawa, H. Nagasawa, J. H. Leech, J. Clin. Invest. 1988, 82, 1560-1566;
33. d) D. E. Goldberg, A. F. G. Slater, R. Beavis, B. Chait, A. Cerami, G. B. Henderson, J. Exp. Med. 1991, 173, 961-969;
34. e) N. D. Gamboa de Dominguez, P. J. Rosenthal, Blood 1996, 87, 4448-4454;
35. f) M. Dua, P. Raphael, P. S. Sijwali, P. J. Rosenthal, M. Hanspal, Mol. Biochem. Parasitol. 2001, 116, 95-99.
36. a) R. G. Ridley, Nature 2002, 415, 686-693;
37. b) G. H. Coombs, D. E. Goldberg, M. Klemba, C. Berry, J. Kay, J. Mottram, Trends Parasitol. 2001, 17, 532-537;
38. c) P. Olliaro, J. Cattani, D. Wirth, JAMA 1996, 275, 230-233.
39. a) X. T. Liang, D. Q. Yu, W. L. Wu, H. C. Deng, Acta Chim. Sin. (Engl. Ed.) 1979, 37, 215-230;
40. b) X. Liang in Advances in Chinese Medicinal Materials (Eds.: H. M. Chang, H. W. Yeung, W. W. Tso, A. Koo), World Scientific, Singapore, 1985, pp. 427-432;
41. c) X. X. Xu, J. Zhu, D.-Z. Huang, W.-S. Zhou, Tetrahedron Lett. 1991, 32, 5785-5788.
42. M. D. Bachi, E. E. Korshin, R. Hoos, A. M. Szpilman, J. Heterocycl. Chem. 2000, 37, 639-646.
43. a) W. Hofheinz, G. Schmid, H. Stohler, Eur. Pat. Appl. 311955, 1989 [Chem. Abstr. 1990, 112, 20999];
44. b) W. Hofheinz, H. Burgin, E. Gocke, C. Jaquet, R. Masciadri, G. Schmid, H. Stohler, H. Urwyler, Trop. Med. Parasitol. 1994, 45, 261-265;
45. c) C. Jaquet, H. R. Stohler, J. Chollet, W. Peters, Trop. Med. Parasitol. 1994, 45, 266-271.
46. M. D. Bachi, E. E. Korshin, P. Ploypradith, J. N. Cumming, S. J. Xie, T. A. Shapiro, G. H. Posner, Bioorg. Med. Chem. Lett. 1998, 8, 903-908.
47. M. D. Bachi, E. E. Korshin, R. Hoos, A. M. Szpilman, P. Ploypradith, S. Xie, T. A. Shapiro, G. H. Posner, J. Med. Chem. 2003, 46, 2516-2533.
48. P. M. O'Neill, N. L. Searle, K. J. Raynes, J. L. Maggs, S. A. Ward, R. C. Storr, B. K. Park, G. H. Posner, Tetrahedron Lett. 1998, 39, 6065-6068.
49. a) T. Tokuyasu, A. Masuyama, M. Nojima, H.-S. Kim, Y. Wataya, Tetrahedron Lett. 2000, 41, 3145-3148;
50. b) T. Tokuyasu, A. Masuyama, M. Nojima, K. J. McCullough, H.-S. Kim, Y. Wataya, Tetrahedron 2001, 57, 5979-5989.
51. H.-S. Kim, K. Begum, N. Ogura, Y. Wataya, T. Tokuyasu, A. Masuyama, M. Nojima, K. J. McCullough, J. Med. Chem. 2002, 45, 4732-4736.
52. P. M. O'Neill, L. P. Bishop, N. L. Searle, J. L. Maggs, S. A. Ward, P. G. Bray, R. C. Storr, B. K. Park, Tetrahedron Lett. 1997, 38, 4263-4266.
53. P. M. O'Neill, L. P. Bishop, N. L. Searle, J. L. Maggs, R. C. Storr, S. A. Ward, B. K. Park, F. Mabbs, J. Org. Chem. 2000, 65, 1578-1582.
54. J. Cazelles, A. Robert, B. Meunier, J. Org. Chem. 1999, 64, 6776-6781.
55. A. M. Szpilman, E. E. Korshin, R. Hoos, G. H. Posner, M. D. Bachi., J. Org. Chem. 2001, 66, 6531-6540.
56. A variety of peptidyl aldehydes are also potent in vitro inhibitors of protozoan CP; see: K.A. Scheidt, W.R. Roush, J.H. McKerrow, P.M. Selzer, E. Hansell, P.J. Rosenthal, Bioorg. Med. Chem. 1998, 6, 2477-2494, and references therein.
57. H. Takikawa, Y. Yamazaki, K. Mori, Eur. J. Org. Chem. 1998, 229.
58. T. Hayashi, Y. Katsuro, M. Kumada, Tetrahedron Lett. 1980, 21, 3915.
59. P. M. O'Neill, M. D. Pugh, A. V. Stachulski, S. A. Ward, J. Davies, B. K. Park, J. Chem. Soc. Perkin Trans. 1 2001, 2682.
60. M. D. Bachi, E. E. Korshin, Synlett 1998, 122-124.
61. E. E. Korshin, R. Hoos, A. M. Szpilman, L. Konstantinovski, G. H. Posner, M. D. Bachi, Tetrahedron 2002, 58, 2449-2469.
62. CCDC 228984 (17c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+ 44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
63. For these modified Pummerer reaction conditions, see: Y. Arroyo-Gomez, J. F. Rodriguez-Amo, M. Santos-Garcia, M. A. Sanz-Tejedor, Tetrahedron: Asymmetry 2000, 11, 789-796.
64. IITPP-induced fragmentation of arteflene (7) has been reported in reference [24].