Mechanism-based design of simple, symmetrical, easily prepared, potent antimalarial endoperoxides

Gary H. Posner; Dasong Wang; Lluïsa González; Xueliang Tao; Jared N. Cumming; Donna Klinedinst; Theresa A. Shapiro

doi:10.1016/0040-4039(95)02329-1

Mechanism-based design of simple, symmetrical, easily prepared, potent antimalarial endoperoxides

Gary H. Posner, Dasong Wang, Lluïsa González, Xueliang Tao, Jared N. Cumming, Donna Klinedinst, Theresa A. Shapiro

School of Medicine

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

51 Scopus citations

Abstract

Mechanism-based design, two-step synthesis, and in vitro antimalarial testing showed thermally stable, crystalline, bicyclic endoperoxides 2a and 2b to be potent antimalarials. Their reduction by FeBr₂ proceeds via oxy-radicals and then carbon radicals that undergo β-scission to form an alkene and a high-valent Fe=O species.

Original language	English (US)
Pages (from-to)	815-818
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	6
DOIs	https://doi.org/10.1016/0040-4039(95)02329-1
State	Published - Feb 5 1996

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(95)02329-1

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abstract = "Mechanism-based design, two-step synthesis, and in vitro antimalarial testing showed thermally stable, crystalline, bicyclic endoperoxides 2a and 2b to be potent antimalarials. Their reduction by FeBr2 proceeds via oxy-radicals and then carbon radicals that undergo β-scission to form an alkene and a high-valent Fe=O species.",

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AU - Posner, Gary H.

AU - Wang, Dasong

AU - González, Lluïsa

AU - Tao, Xueliang

AU - Cumming, Jared N.

AU - Klinedinst, Donna

AU - Shapiro, Theresa A.

PY - 1996/2/5

Y1 - 1996/2/5

N2 - Mechanism-based design, two-step synthesis, and in vitro antimalarial testing showed thermally stable, crystalline, bicyclic endoperoxides 2a and 2b to be potent antimalarials. Their reduction by FeBr2 proceeds via oxy-radicals and then carbon radicals that undergo β-scission to form an alkene and a high-valent Fe=O species.

AB - Mechanism-based design, two-step synthesis, and in vitro antimalarial testing showed thermally stable, crystalline, bicyclic endoperoxides 2a and 2b to be potent antimalarials. Their reduction by FeBr2 proceeds via oxy-radicals and then carbon radicals that undergo β-scission to form an alkene and a high-valent Fe=O species.

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JO - Tetrahedron Letters

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IS - 6

ER -

Mechanism-based design of simple, symmetrical, easily prepared, potent antimalarial endoperoxides

Abstract

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