Antimalarial sulfide, sulfone, and sulfonamide trioxanes

Gary H. Posner; John P. Maxwell; Hardwin O'Dowd; Mikhail Krasavin; Suji Xie; Theresa A. Shapiro

doi:10.1016/S0968-0896(00)00079-1

Antimalarial sulfide, sulfone, and sulfonamide trioxanes

Gary H. Posner, John P. Maxwell, Hardwin O'Dowd, Mikhail Krasavin, Suji Xie, Theresa A. Shapiro

School of Medicine

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

37 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	1361-1370
Number of pages	10
Journal	Bioorganic and Medicinal Chemistry
Volume	8
Issue number	6
DOIs	https://doi.org/10.1016/S0968-0896(00)00079-1
State	Published - Jun 2000

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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title = "Antimalarial sulfide, sulfone, and sulfonamide trioxanes",

abstract = "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.",

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AU - Posner, Gary H.

AU - Maxwell, John P.

AU - O'Dowd, Hardwin

AU - Krasavin, Mikhail

AU - Xie, Suji

AU - Shapiro, Theresa A.

N1 - Funding Information: We thank the NIH (AI-34885 and NCRR grant #RR00052) and the Burroughs Wellcome Fund for financial support.

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Antimalarial sulfide, sulfone, and sulfonamide trioxanes

Abstract

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