New amino endoperoxides belonging to the antimalarial G-factor series

European Journal of Organic Chemistry

Volumn , Issue 19, 2007, Pages 3095-3101

  Givelet, Cécile ^a   Bernat, Virginie ^a   Danel, Mathieu ^a   André Barrès, Christiane ^a   Vial, Henri ^b  

^a Université Paul Sabatier Toulouse III   (France)

^b UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

1,2 dioxetane; Autoxidation; Endoperoxide; Hexacoordinate fluorosilicon complex; Malaria

Indexed keywords

EID: 34447304676     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700086     Document Type: Article

References (20)

1. A. R. Renslo, J. H. McKerrow, Nat. Chem. Biol. 2006, 2, 701-710.
2. P. M. O'Neill, G. H. Posner, J. Med. Chem. 2004, 47, 2945-2964 and references cited therein.
3. P. M. O'Neill, S. L. Rawe, K. Borstnik, A. Miller, Q. A. Ward, P. G. Bray, J. Davies, C. H. Oh, G. H. Posner, ChemBioChem 2005, 6, 2048-2054.
4. G. H. Posner, J. N. Cumming, S.-H. Woo, P. Ploypradith, S. Xie, T. Shapiro, J. Med. Chem. 1998, 41, 940-951.
5. C. Singh, H. Malik, S. K. Puri, J. Med. Chem. 2006, 49, 2794-2803.
6. J. L. Vennerstrom, S. Arbe-Barnes, R. Brun, S. A. Charman, F. C. K. Chiu, J. Chollet, Y. Dong, A. Dorn, D. Hunziker, H. Matile, K. McIntosh, M. Padmanilayam, J. SantoTomas, C. Scheurer, B. Scorneaux, Y. Tang, H. Urwyler, S. Wittlin, W. N. Charman, Nature 2004, 430, 900-904.
7. G. H. Posner, H. O. Dowd, P. Ploypradith, J. N. Cumming, S. Xie, T. Shapiro, J. Med. Chem. 1998, 41, 2164-2167.
8. M. D. Bachi, E. E. Korshin, R. Hoos, A. M. Szpilman, P. Ploypradith, S. Xie, T. Shapiro, G. Posner, J. Med. Chem. 2003, 46, 2516-2533.
9. P. M. O'Neill, P. A. Stocks, M. D. Pugh, N. C. Araujo, E. E. Korshin, J. F. Bickley, S. A. Ward, P. G. Bray, E. Pasini, J. Davies, E. Verissimo, M. D. Bachi, Angew. Chem. Int. Ed. 2004, 43, 4193-4197.
10. E. Ghisaberti, Phytochemistry 1996, 41, 7-22.
11. F. Najjar, M. Baltas, L. Gorrichon, Y. Moreno, T. Tzedakis, H. Vial, C. André-Barrès, Eur. J. Org. Chem. 2003, 17, 3335-3343.
12. F. Najjar, L. Gorrichon, M. Baltas, H. Vial, T. Tzedakis, C. André-Barrès, Bioorg. Med. Chem. Lett. 2003, 14, 1433-1436.
13. C. André-Barrès, F. Najjar, A.-L. Bottalla, S. Massou, C. Zedde, M. Baltas, L. Gorrichon, J. Org. Chem. 2005, 70, 6921-6924.
14. F. Najjar, L. Gorrichon, M. Baltas, C. André-Barrès, H. Vial, Org. Biomol. Chem. 2005, 3, 1612-1614.
15. 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.
16. R. K. Haynes, W. Y. Ho, H.-W. Chan, B. Fugmann, J. Stetter, S. L. Croft, L. Vivas, W. Peters, B. L. Robinson, Angew. Chem. Int. Ed. 2004, 43, 1381-1385.
17. R. K. Haynes, B. Fugmann, J. Stetter, K. Rieckmann, H.-D. Heilmann, H.-W. Chan, M.-K. Cheung, W.-L. Lam, H.-N. 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. Gerish, M. Radtke, G. Schmuck, W. Steinke, U. Wollborn, K. Schmeer, A. Römer, Angew. Chem. Int. Ed. 2006, 45, 2082-2088.
18. F. Najjar, C. André-Barrès, R. Lauricella, L. Gorrichon, B. Tuccio, Tetrahedron Lett. 2005, 46, 2117-2119.
19. Molecular mechanic calculations were run with the Insight (2000) program with use of the Discover 3 calculation mode (Accelerys, San Diego, USA). Consistence valence force fields (CVFF) were used. Energetically optimised conformations were determined by sampling structures during molecular dynamic simulations. They were run for 10 ps at 800 K by the NVT method, with a 1 fs time step. From the energy/time curves, six to seven minima were chosen and minimised. The same iterative operations (dynamic simulations and minimisation) were undertaken on these minima until no energy variation occurred. For each minimisation rms < 0.001.
20. C. R. Chuit, J. P. Corriu, C. Reye, J. C. Young, Chem. Rev. 1993, 93, 1371.