Antimalarial sulfide, sulfone, and sulfonamide trioxanes.
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.
Posner
G H
GH
Department of Chemistry, School of Arts and Sciences, The Johns Hopkins University, Baltimore, MD 21218, USA.
Maxwell
J P
JP
O'Dowd
H
H
Krasavin
M
M
Xie
S
S
Shapiro
T A
TA
D000962:Antimalarials / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D013057:Spectrum Analysis; D013329:Structure-Activity Relationship; D013440:Sulfides / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry; D013450:Sulfones / Q000737:chemistry
D000962:Antimalarials; D013440:Sulfides; D013449:Sulfonamides; D013450:Sulfones