MECHANISM-BASED DESIGN OF SIMPLE, SYMMETRICAL, EASILY PREPARED, POTENT ANTIMALARIAL ENDOPEROXIDES

Authors
POSNER GH WANG DS GONZALEZ L TAO XL CUMMING JN KLINEDINST D SHAPIRO TA
Citation
Gh. Posner et al., MECHANISM-BASED DESIGN OF SIMPLE, SYMMETRICAL, EASILY PREPARED, POTENT ANTIMALARIAL ENDOPEROXIDES, Tetrahedron letters, 37(6), 1996, pp. 815-818
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
6
Year of publication
1996
Pages
815 - 818
Database
ISI
SICI code
0040-4039(1996)37:6<815:MDOSSE>2.0.ZU;2-W
Abstract
Mechanism-based design, two-step synthesis, and in vitro antimalarial testing showed thermally stable, crystalline, bicyclic endoperoxides 2 a and 2b to be potent antimalarials. Their reduction by FeBr2 proceeds via oxy-radicals and then carbon radicals that undergo beta-scission to form an alkene and a high-valent Fe=O species.