288571-51-7Relevant academic research and scientific papers
Antimalarial sulfide, sulfone, and sulfonamide trioxanes
Posner, Gary H.,Maxwell, John P.,O'Dowd, Hardwin,Krasavin, Mikhail,Xie, Suji,Shapiro, Theresa A.
, p. 1361 - 1370 (2007/10/03)
A series of trioxanes featuring sulfide, sulfone, and sulfonamide substituents in diverse positions has been prepared. Structure-activity relationship (SAR) generalizations highlight two major factors controlling the antimalarial potency of these new chemical entities: (1) the proximity of the sulfur-containing substituent to the crucial peroxide bond and (2) the oxidation state of the sulfur-containing substituent. Generally, sulfones are more antimalarially potent than the corresponding sulfides. Copyright (C) 2000 Elsevier Science Ltd.
Antimalarial sulfone trioxanes
Posner, Gary H.,O'Dowd, Hardwin,Caferro, Thomas,Cumming, Jared N.,Ploypradith, Poonsakdi,Xie, Suji,Shapiro, Theresa A.
, p. 2273 - 2276 (2007/10/03)
A series of new sulfide and sulfone 1,2,4-trioxanes was prepared in only a few steps from commercial reactants. The sulfone trioxanes were found to have higher in vitro antimalarial potencies than the sulfides, with 12β- arylsulfone trioxanes 1β being from 1/3 to 1/4 as potent as the complex natural antimalarial trioxane artemisinin (2). A tentative chemical mechanism is proposed to account for the great difference in antimalarial activity of the 12α- vs. 12β-sulfide trioxanes.
