Antimalarial sulfide trioxanes: a revision of mechanism

Posner GH; Chang W

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Antimalarial sulfide trioxanes: a revision of mechanism

机译：抗疟硫化物三氧化：修订机制

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The mechanism by which an antimalarially inactive sulfanyl trioxane reacts with ferrous iron is revised. Although originally proposed to involve a short-lived high-valent iron-oxo intermediate, the revised mechanism involves FeBr2 acting as a weak Lewis acid promoting intramolecular redox chemistry between the peroxide unit and the resident sulfanyl sulfur atom; one of the peroxide oxygen atoms is transferred intramolecularly to the neighboring sulfide sulfur atom, oxidizing it into a sulfoxide and reducing the trioxane into a non-peroxidic dioxolane. This facile ferrous iron-triggered conversion of the parent 1,2,4-trioxane sulfide into the corresponding 1,3-dioxolane sulfoxide accounts for the observed lack of antimalarial activity of the parent sulfanyl trioxane without invoking the intermediacy of a high-valent iron-oxo species.

机译：修订抗体型无活性磺基三恶烷的机理与亚铁铁进行了修订。虽然最初提出涉及短暂的高价铁 - 氧中中间体，但修正机制涉及FEBR2作为促进过氧化物单元和常磺酰硫原子之间的分子内氧化还原化学的弱路易斯酸; 将过氧化氧原子中的一种分体转移到相邻的硫化物硫原子中，将其氧化成亚砜并将三恶烷还原成非过氧化二氧氧氧氧烷。这种容易铁铁触发的母体1,2,4-三恶烷硫化物转化为相应的1,3-二氧戊烷亚砜，用于观察到母体磺酰基三恶烷的缺乏抗疟疾活性而不调用高价铁的介质 - 过量的物种。

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来源
《Journal of Physical Organic Chemistry》 |2008年第8期|共3页
作者
Posner GH; Chang W;
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作者单位

Johns Hopkins Univ Dept Chem Sch Arts &

Sci Baltimore MD 21218 USA.;

Johns Hopkins Univ Dept Chem Sch Arts &

Sci Baltimore MD 21218 USA.;

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原文格式 PDF
正文语种 eng
中图分类有机化学一般性问题;
关键词
peroxides; mechanism of action; intramolecular redox chemistry;

机译：过氧化物;作用机制;分子内氧化还原化学;

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专利

1. Antimalarial sulfide trioxanes: a revision of mechanism [J] . Posner GH, Chang W Journal of Physical Organic Chemistry . 2008,第7a8期

机译：抗疟硫化物三氧化：修订机制
2. Antimalarial sulfide, sulfone, and sulfonamide trioxanes. [J] . Posner GH, Maxwell JP, ODowd H, Bioorganic and medicinal chemistry . 2000,第6期

机译：抗疟疾硫化物，砜和磺酰胺三恶烷。
3. Enantiomeric 1,2,4-Trioxanes Display Equivalent in vitro Antimalarial Activity Versus Plasmodium falciparum Malaria Parasites: Implications for the Molecular Mechanism of Action of the Artemisinins [J] . Paul M.ONeill, Sarah L.Rawe, Alison Miller, Chembiochem: A European journal of chemical biology . 2005,第11期

机译：对映体1,2,4-三恶烷显示等效的体外抗疟活性与恶性疟原虫疟疾寄生虫：对青蒿素的分子作用机理的影响。
4. Mechanisms of beta-Hematin Crystallization and Inhibition by Antimalarial Growth Modifiers [C] . Katy N. Olafson, Peter G. Vekilov, Jeffrey D. Rimer AIChE Annual Meeting . 2014

机译：β-血红素结晶和抗疟生生长改性剂的抑制机制
5. Synthesis of potent analogs of the antimalarial 1,2,4-trioxane natural product artemisinin, and, mechanistic studies directed towards elucidation of the mechanism(s) of antimalarial action of artemisinin and its 1,2,4-trioxane analogs. [D] . Cumming, Jared Nathaniel. 1998

机译：合成抗疟疾的1,2,4-三恶烷天然产物青蒿素的有效类似物，以及旨在阐明青蒿素及其1,2,4-三恶烷类似物的抗疟作用机理的机理研究。
6. Synthesis and Antimalarial Efficacy of Two-Carbon Linked Artemisinin-Derived Trioxane Dimers in Combination with Known Antimalarial Drugs [O] . Bryan T. Mott, Abhai Tripathi, Maxime A. Siegler, -1

机译：二碳的合成和抗疟疾功效挂钩青蒿素衍生三聚甲醛二聚体与已知抗疟药
7. Synthesis, in vitro and in vivo antimalarial assessment of sulfide, sulfone and vinyl amide-substituted 1,2,4-trioxanes prepared via thiol-olefin co-oxygenation (TOCO) of allylic alcohols. [O] . Amewu, Richard, Gibbons, Peter, Mukhtar, Amira, 2010

机译：通过烯丙醇的硫醇-烯烃共加氧（TOCO）制备的硫化物，砜和乙烯基酰胺取代的1,2,4-三恶烷的合成，体外和体内抗疟疾评估。
8. In vitro Activities of and Mechanisms of Resistance to Antifol Antimalarial Drugs [R] . Milhous, W. K., Weatherly, N. F., Bowdre, J. H., 1985

机译：抗人抗癫痫药物的体外活性及其机制

Antimalarial sulfide trioxanes: a revision of mechanism

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