Spiroadamantyl 1,2,4-trioxolane, 1,2,4-trioxane, and 1,2,4-trioxepane pairs: Relationship between peroxide bond iron(II) reactivity, heme alkylation efficiency, and antimalarial activity

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 16, 2009, Pages 4542-4545

  Wang, Xiaofang ^a   Creek, Darren J ^b   Schiaffo, Charles E ^c   Dong, Yuxiang ^a   Chollet, Jacques ^d   Scheurer, Christian ^d   Wittlin, Sergio ^d   Charman, Susan A ^b   Dussault, Patrick H ^c   Wood, James K ^e   Vennerstrom, Jonathan L ^a  

^a NEBRASKA MEDICAL CENTER   (United States)

^b MONASH UNIVERSITY   (Australia)

^c UNIVERSITY OF NEBRASKA LINCOLN   (United States)

^d SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^e UNIVERSITY OF NEBRASKA AT OMAHA   (United States)

Author keywords

1,2,4 Trioxane; 1,2,4 Trioxepane; 1,2,4 Trioxolane; Antimalarial; Artemisinin; Peroxide

Indexed keywords

1,2,4 TRIOXANE DERIVATIVE; 1,2,4 TRIOXEPANE DERIVATIVE; 1,2,4 TRIOXOLANE DERIVATIVE; ARTEMISININ; FERROUS ION; FERROUS SULFATE; HEME; UNCLASSIFIED DRUG;

ALKYLATION; ANTIMALARIAL ACTIVITY; ARTICLE; DRUG STRUCTURE; IC 50;

ALKYLATION; ANIMALS; ANTIMALARIALS; COMPUTER SIMULATION; FERRIC COMPOUNDS; FERROUS COMPOUNDS; HEME; HETEROCYCLIC COMPOUNDS; MICE; PARASITIC SENSITIVITY TESTS; PEROXIDES;

EID: 67651083553     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.07.013     Document Type: Article

References (30)

1. White N.J. Science 320 (2008) 330
2. Jefford C.W. Curr. Med. Chem. 8 (2001) 1803
3. Meshnick S.R. Int. J. Parasitol. 32 (2002) 1655
4. O'Neill P.M., and Posner G.H. J. Med. Chem. 47 (2004) 2945
5. Kaiser M., Wittlin S., Nehrbass-Stuedli A., Dong Y., Wang X., Hemphill A., Matile H., Brun R., and Vennerstrom J.L. Antimicrob. Agents Chemother. 51 (2007) 2991
6. Robert A., Benoit-Vical F., Claparols C., and Meunier B. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 13676
7. Casteel D.A., Peri S.P., and Gerena L. Bioorg. Med. Chem. Lett. 3 (1993) 1707
8. Tang Y., Dong Y., and Vennerstrom J.L. Med. Res. Rev. 24 (2004) 425
9. Vennerstrom J.L., Arbe-Barnes S., Brun R., Charman S.A., Chiu F.C.K., Chollet J., Dong Y., Dorn A., Hunziker D., Matile H., McIntosh K., Padmanilayam M., Santo Tomas J., Scheurer C., Scorneaux B., Tang Y., Urwyler H., Wittlin S., and Charman W.N. Nature 430 (2004) 900
10. +): 301.1804; found 301.1809.
11. Keul H. Chem. Ber. 108 (1975) 1207
12. Griesbaum K., Liu X., Kassiaris A., and Scherer M. Liebigs Ann. Recl. (1997) 1381
13. Konakahara T., Matsuki M., Sugimoto S., and Sato K. J. Chem. Soc., Perkin Trans. 1 (1987) 1489
14. Dong Y., and Vennerstrom J.L. J. Org. Chem. 63 (1998) 8582
15. Dong Y., Chollet J., Matile H., Charman S.A., Chiu F.C.K., Charman W.N., Scorneaux B., Urwyler H., Santo Tomas J., Scheurer C., Snyder C., Dorn A., Wang X., Karle J.M., Tang Y., Wittlin S., Brun R., and Vennerstrom J.L. J. Med. Chem. 48 (2005) 4953
16. Ogata Y., Sawaki Y., and Shimizu H. J. Org. Chem. 43 (1978) 1760
17. Kagan J., and Przybytek J.T. Tetrahedron 29 (1973) 1163
18. Kharasch M.S., Fono A., and Nudenberg W. J. Org. Chem. 15 (1950) 748
19. Kim H.-S., Tsuchiya K., Shibata Y., Wataya Y., Ushigoe Y., Araki M., Nojima M., and McCullough K.J. J. Chem. Soc., Perkin Trans. 1 (1999) 1867
20. Tang Y., Dong Y., Wang X., Sriraghavan K., Wood J.K., and Vennerstrom J.L. J. Org. Chem. 70 (2005) 5103
21. Bourhani Z., and Malkov A. Chem. Commun. (2005) 4592
22. Tokuyasu T., Kunikawa S., Masuyama A., and Nojima M. Org. Lett. 4 (2002) 3595
23. Jin H., Liu H., Zhang Q., and Wu Y. J. Org. Chem. 70 (2005) 4240
24. Kornblum N., and DeLaMare H.E. J. Am. Chem. Soc. 73 (1951) 880
25. Creek D.J., Chiu F.C.K., Prankerd R.J., Charman W.N., and Charman S.A. J. Pharm. Sci. 94 (2005) 1820
26. Creek D.J., Charman W.N., Chiu F.C.K., Prankerd R.J., McCullough K.J., Dong Y., Vennerstrom J.L., and Charman S.A. J. Pharm. Sci. 96 (2007) 2945
27. Wang X., Dong Y., Wittlin S., Creek D., Chollet J., Charman S.A., Santo Tomas J., Scheurer C., Snyder C., and Vennerstrom J.L. J. Med. Chem. 50 (2007) 5840
28. ax) is 0.280 and 1.71 kcal/mol, respectively.
29. Amewu R., Stachulski A.V., Berry N.G., Ward S.A., Davies J., Labat G., Rossignol J.-F., and O'Neill P.M. Bioorg. Med. Chem. Lett. 16 (2006) 6124
30. Creek D.J., Charman W.N., Chiu F.C.K., Prankerd R.J., Dong Y., Vennerstrom J.L., and Charman S.A. Antimicrob. Agents Chemother. 52 (2008) 1291