An efficient route into synthetically challenging bridged achiral 1,2,4,5-tetraoxanes with antimalarial activity

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 5, 2008, Pages 1720-1724

  Ellis, Gemma L ^a   Amewu, Richard ^a   Hall, Charlotte ^b   Rimmer, Karen ^b   Ward, Steven A ^b   O'Neill, Paul M ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b LIVERPOOL SCHOOL OF TROPICAL MEDICINE   (United Kingdom)

Author keywords

1,2,4 Trioxane; Antimalarial; Artemisinin; Plasmodium falciparum; Tetraoxane

Indexed keywords

ANTIMALARIAL AGENT; ARTEMETHER; ARTEMISININ; PEROXIDE; PROPANE; SILVER DERIVATIVE; TETRAOXANE DERIVATIVE;

ALKYLATION; ANTIMALARIAL ACTIVITY; ARTICLE; CATALYSIS; CHIRALITY; DRUG POTENCY; DRUG SYNTHESIS; IC 50; METHODOLOGY; NONHUMAN; PLASMODIUM FALCIPARUM; WITTIG REACTION;

ANIMALS; ANTIMALARIALS; ARTEMISININS; MOLECULAR STRUCTURE; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAOXANES;

PLASMODIUM FALCIPARUM;

EID: 39849083194     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.01.053     Document Type: Article

References (38)

1. Haynes R.K., and Krishna S. Microbes Infect. 6 (2004) 1339
2. Haynes R.K. Curr. Top. Med. Chem. 6 (2006) 509
3. Haynes R.K. Curr. Opin. Infect. Dis. 14 (2001) 719
4. O'Neill P.M., and Posner G.H. J. Med. Chem. 47 (2004) 2945
5. Vennerstrom J.L. J. Med. Chem. 32 (1989) 64
6. Vennerstrom J.L., Fu H.N., Ellis W.Y., Ager A.L., Wood J.K., et al. J. Med. Chem. 35 (1992) 3023
7. Vennerstrom J.L., Arbe-Barnes S., Brun R., Charman S.A., Chiu F.C.K., et al. Nature 430 (2004) 900
8. Nonami Y., Tokuyasu T., Masuyama A., Nojima M., McCullough K.J., et al. Tetrahedron Lett. 41 (2000) 4681
9. Tokuyasu T., Masuyama A., Nojima M., Kim H.S., and Wataya Y. Tetrahedron Lett. 41 (2000) 3145
10. Opsenica R., Angelovski G., Pocsfalvi G., Juranic Z., Zizak Z., et al. Bioorg. Med. Chem. 11 (2003) 2761
11. Dong Y.X., Chollet J., Matile H., Charman S.A., Chiu F.C.K., et al. J. Med. Chem. 48 (2005) 4953
12. Tang Y.Q., Dong Y.X., Wittlin S., Charman S.A., Chollet J., et al. Bioorg. Med. Chem. Lett. 17 (2007) 1260
13. Griesbeck A.G., and El-Idreesy T.T. J. Chin. Chem. Soc.-TAIP 53 (2006) 1469
14. Griesbeck A.G., El-Idreesy T.T., and Bartoschek A. Pure Appl. Chem. 77 (2005) 1059
15. Benoit-Vical F., Lelievre J., Berry A., Deymier C., Dechy-Cabaret O., et al. Antimicrob. Agents. Chemother. 51 (2007) 1463
16. Dong Y.X., and Vennerstrom J.L. Abstr. Pap. Am. Chem. Soc. 230 (2005) U2617
17. Jin H.X., Zhang Q., Kim H.S., Wataya Y., Liu H.H., et al. Tetrahedron 62 (2006) 7699
18. Tang Y.Q., Dong Y.X., Wang X.F., Sriraghavan K., Wood J.K., et al. J. Org. Chem. 70 (2005) 5103
19. Vennerstrom, J. L.; Dong, Y. C.; Chollet, J.; Matile, H. U.S. Patent 6,489,199, 2001.
20. Dong Y.X., and Vennerstrom J.L. J. Org. Chem. 63 (1998) 8582
21. Dong Y.X., Matile H., Chollet J., Kaminsky R., Wood J.K., et al. J. Med. Chem. 42 (1999) 1477
22. Tsuchiya K., Hamada Y., Masuyama A., Nojima M., McCullough K.J., et al. Tetrahedron Lett. 40 (1999) 4077
23. Vennerstrom J.L., Dong Y.X., Andersen S.L., Ager A.L., Fu H.N., et al. J. Med. Chem. 43 (2000) 2753
24. Opsenica D., Pocsfalvi G., Milhous W.K., and Solaja B.A. J. Serb. Chem. Soc. 67 (2002) 465
25. Iskra J., Bonnet-Delpon D., and Begue J.P. Tetrahedron Lett. 44 (2003) 6309
26. Terent'ev A.O., Kutkin A.V., Starikova Z.A., Antipin M.Y., Ogibin Y.N., et al. Synthesis-Stuttgart (2004) 2356
27. Masuyama A., Wu J.M., Nojima M., Kim H.S., and Wataya Y. Mini-Rev. Med. Chem. 5 (2005) 1035
28. Amewu R., Stachulski A.V., Ward S.A., Berry N.G., Bray P.G., et al. Org. Biomol. Chem. 4 (2006) 4431
29. Amewu R., Stachulski A.V., Ward S.A., Berry N.G., Bray P.G., et al. Org. Biomol. Chem. 5 (2007) 708
30. Kim H.S., Nagai Y., Ono K., Begum K., Wataya Y., et al. J. Med. Chem. 44 (2001) 2357
31. 3N, found 338.1574. Elemental analysis C: 56.99, H: 7.91, N: 4.39 (required values C: 57.13, H: 7.99, N: 4.39).
32. Zmitek K., Zupan M., Stavber S., and Iskra J. Org. Lett. 8 (2006) 2491
33. 4N, found 296.18672.
34. 6Na, found 359.1460.
35. 3N, found 376.17470.
36. http://146.107.217.178/lab/alogps/.
37. http://www.molinspiration.com/cgi-bin/properties.
38. Smilkstein M., Sriwilaijaroen N., Kelly J.X., Wilairat P., and Riscoe M. Antimicrob. Agents Chemother. 48 (2004) 1803