Antimalarial sulfide trioxanes: A revision of mechanism

Journal of Physical Organic Chemistry

Volumn 21, Issue 7-8, 2008, Pages 538-540

  Posner, Gary H ^a   Chang, Wonsuk ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

Intramolecular redox chemistry; Mechanism of action; Peroxides

Indexed keywords

MECHANISMS; ZINC SULFIDE;

FERROUS IRON; HIGH-VALENT IRON(IV); TRIOXANE;

IRON;

EID: 46949086211     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1307     Document Type: Conference Paper

References (16)

1. A. R. Butler, Y. Wu, Chem. Soc. Rev. 1992, 21, 85-90.
2. S. Kamchonwongpaisan, S. R. Meshnick, Gen. Pharmacol. 1996, 27, 587-592.
3. S. R. Meshnick, A. Thomas, A. Ranz, C. M. Xu, H. Z. Pan, Mol. Biochem. Parasitol. 1991, 49, 181-189.
4. A. Robert, F. Benoit-Vical, B. Meunier, Coord. Chem. Rev. 2005, 249, 1927-1936.
5. L. Messori, C. Gabbiani, A. Casini, M. Siragusa, F. F. Vincieri, A. R. Bilia, Bioorg. Med. Chem. 2006, 14, 2972-2977.
6. G. H. Posner, C. H. Oh, J. Am. Chem. Soc. 1992, 114, 8328-8329.
7. W. M. Wu, Y. K. Wu, Y. L. Wu, Z. J. Yao, C. M. Zhou, Y. Li, F. Shan, J. Am. Chem. Soc. 1998, 120, 3316-3325.
8. G. H. Posner, P. M. O'Neill, Acc. Chem. Res. 2004, 37, 397-404.
9. P. M. O'Neill, G. H. Posner, J. Med. Chem. 2004, 47, 2945-2964.
10. For argument against the intermediacy of a high-valent iron-oxo species, see A. Robert, O. Dechy-Cabaret, J. Cazelles, B. Meunier, Acc. Chem. Res. 2002, 35, 167-174.
11. S. Kapetanaki, C. Varotsis, FEBS Lett. 2000, 474, 238-241.
12. G. H. Posner, J. N. Cumming, P. Ploypradith, C. H. Oh, J. Am. Chem. Soc. 1995, 117, 5885-5886.
13. G. H. Posner, H. O'Dowd, T. Caferro, J. N. Cumming, P. Ploypradith, S. Xie, T. A. Shapiro, Tetrahedron Lett. 1998, 39, 2273-2276.
14. The equilibrium geometry at ground state was calculated using the Hartree-Fock split-valence (3-21G) method of Spartan '02.
15. For iron salts acting as Lewis acids toward trioxanes, see R. K. Haynes, S. C. Vonwiller, Tetrahedron Lett. 1996, 37, 257-260.
16. S. Oae, in The Organic Chemistry of Sulfur (Ed.: S. Oae) Plenum, NY, 1977, 385-390.