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

被引：8

作者：

CASTEEL, DA ^{[1
]}

PERI, SP ^{[1
]}

GERENA, L ^{[1
]}

机构：

[1] WALTER REED ARMY INST RES,DIV EXPTL THERAPEUT,WASHINGTON,DC 20307

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1993年 / 3卷 / 08期

关键词：

D O I：

10.1016/S0960-894X(00)80047-5

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The title compound was prepared from the known 6-tetrahydrooxepanol by formation of the 6-mesylate followed by treatment with acidic methanol to yield the methyl acetal. Reaction of 2-methoxy-6-mesyloxytetrahydrooxepane with anhydrous hydrazine followed by treatment with 30 hydrogen peroxide and sodium peroxide provided the diastereomeric mixture of 6-hydroperoxides. The hydroperoxides cyclized upon treatment with acid to give trioxabicyclo[2.2.3]bicyclononane. The bridged bicyclic trioxane exhibited only marginal antimalarial activity.

引用

页码：1707 / 1710

页数：4

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