Antimalarial sulfone trioxanes

Gary H. Posner; Hardwin O'Dowd; Thomas Caferro; Jared N. Cumming; Poonsakdi Ploypradith; Suji Xie; Theresa A. Shapiro

doi:10.1016/S0040-4039(98)00290-1

Antimalarial sulfone trioxanes

Gary H. Posner, Hardwin O'Dowd, Thomas Caferro, Jared N. Cumming, Poonsakdi Ploypradith, Suji Xie, Theresa A. Shapiro

School of Medicine

Research output: Contribution to journal › Article › peer-review

40 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	2273-2276
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	16
DOIs	https://doi.org/10.1016/S0040-4039(98)00290-1
State	Published - Apr 16 1998

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Antimalarial sulfone trioxanes",

abstract = "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.",

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AU - Posner, Gary H.

AU - O'Dowd, Hardwin

AU - Caferro, Thomas

AU - Cumming, Jared N.

AU - Ploypradith, Poonsakdi

AU - Xie, Suji

AU - Shapiro, Theresa A.

N1 - Funding Information: Wellcome Fund for financial support.

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Y1 - 1998/4/16

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AB - 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.

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Antimalarial sulfone trioxanes

Abstract

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