SYNTHESIS AND ANTIMALARIAL EVALUATION OF 2,3,5-TRIOXABICYCLO[2.2.3]NONANE, A MODEL FOR THE PUTATIVE PHARMACOPHORE OF ARTEMISININ

Authors
CASTEEL DA PERI SP GERENA L
Citation
Da. Casteel et al., SYNTHESIS AND ANTIMALARIAL EVALUATION OF 2,3,5-TRIOXABICYCLO[2.2.3]NONANE, A MODEL FOR THE PUTATIVE PHARMACOPHORE OF ARTEMISININ, Bioorganic & medicinal chemistry letters, 3(8), 1993, pp. 1707-1710
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
8
Year of publication
1993
Pages
1707 - 1710
Database
ISI
SICI code
0960-894X(1993)3:8<1707:SAAEO2>2.0.ZU;2-A
Abstract
The title compound was prepared from the known 6-tetrahydrooxepanol by formation of the 6-mesylate followed by treatment with acidic methano l to yield the methyl acetal. Reaction of 2-methoxy-6-mesyloxytetrahyd rooxepane with anhydrous hydrazine followed by treatment with 30 hydro gen peroxide and sodium peroxide provided the diastereomeric mixture o f 6-hydroperoxides. The hydroperoxides cyclized upon treatment with ac id to give trioxabicyclo[2.2.3]bicyclononane. The bridged bicyclic tri oxane exhibited only marginal antimalarial activity.