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新型6-烷基乙烯基/芳基烷基乙烯基取代的1,2,4-三恶烷的合成及其对小鼠耐多药疟疾的活性研究

Synthesis of new 6-alkylvinyl/arylalkylvinyl substituted 1,2,4-trioxanes active against multidrug-resistant malaria in mice.

作者信息

Singh Chandan, Gupta Nitin, Puri Sunil K

机构信息

Division of Medicinal & Process Chemistry, Central Drug Research Institute, Lucknow 226001, India.

出版信息

Bioorg Med Chem. 2004 Nov 1;12(21):5553-62. doi: 10.1016/j.bmc.2004.08.005.

DOI:10.1016/j.bmc.2004.08.005
PMID:15465332
Abstract

3-Alkyl/arylalkyl substituted 2-butenols 9, 10, 23a-d undergo regiospecific photooxygenation to furnish beta-hydroxyhydroperoxides 11, 12, 24a-d, respectively, in reasonable yields. Acid catalyzed condensation of 11, 12, 24a-d with various ketones furnish new 1,2,4-trioxanes 13-18, 25a-d, 26a-d, 27a-d in good yields. Several of these trioxanes show promising antimalarial activity against multidrug-resistant Plasmodium yoelii in mice by oral and intramuscular routes.

摘要

3-烷基/芳基烷基取代的2-丁烯醇9、10、23a-d进行区域特异性光氧化反应，分别以合理的产率生成β-羟基氢过氧化物11、12、24a-d。11、12、24a-d与各种酮在酸催化下缩合，以良好的产率生成新的1,2,4-三恶烷13 - 18、25a-d、26a-d、27a-d。其中几种三恶烷通过口服和肌肉注射途径对小鼠体内耐多药的约氏疟原虫显示出有前景的抗疟活性。

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