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Synthesis, iron(II)-induced cleavage and in vivo antimalarial efficacy of 10-(2-hydroxy-1-naphthyl)-deoxoqinghaosu(-deoxoartemisinin)
Alternative Title10-(2-羟基-1-奈基)-脱氧青蒿素的合成, 亚铁诱导的裂解及体内抗疟活性
Wang DY(王东业); Wu YK(伍贻康); Wu YL(吴毓林); Li Y(李英); Shan F(山峰)
1999
Source PublicationJ. Chem. Soc.-Perkin Trans. 1
ISSN0300-922X
Pages1827-1831
AbstractA convenient methodology for attaching an acid-stable UV chromophore onto the qinghaosu (artemisinin) framework with readily available dihydroqinghaosu acetate as the starting material is presented. The resulting derivatives of deoxoqinghaosu may be used as a sensitive probe in the mechanistic and biological/pharmacological investigations. As the first application of the present methodology, naphth-2-ol is attached to qinghaosu nucleus through a carbon-carbon single bond by a boron trifluoride-catalyzed Friedel-Crafts alkylaiton. A previously undetected reacemizaiton at C-9 mediated by an enol ethyer under the reaction conditions (BF=3.Oet=2,CH=2.Cl2)that have been widely used for preparing C-10 derivatives of dihydroqinghaosu is obsered. The knowledgegainedfrom the present work may assist the rational design of new trioxane-type antimalarial agents.
Subject Area生命有机化学
Department中国科学院上海有机化学研究所生命有机国家开放实验室; 上海药物所
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Indexed BySCI
Language英语
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/13950
Collection生命有机化学国家重点实验室
Corresponding AuthorWu YK(伍贻康); Wu YL(吴毓林); Li Y(李英)
Recommended Citation
GB/T 7714
Wang DY,Wu YK,Wu YL,et al. Synthesis, iron(II)-induced cleavage and in vivo antimalarial efficacy of 10-(2-hydroxy-1-naphthyl)-deoxoqinghaosu(-deoxoartemisinin)[J]. J. Chem. Soc.-Perkin Trans. 1,1999:1827-1831.
APA 王东业,伍贻康,吴毓林,李英,&山峰.(1999).Synthesis, iron(II)-induced cleavage and in vivo antimalarial efficacy of 10-(2-hydroxy-1-naphthyl)-deoxoqinghaosu(-deoxoartemisinin).J. Chem. Soc.-Perkin Trans. 1,1827-1831.
MLA 王东业,et al."Synthesis, iron(II)-induced cleavage and in vivo antimalarial efficacy of 10-(2-hydroxy-1-naphthyl)-deoxoqinghaosu(-deoxoartemisinin)".J. Chem. Soc.-Perkin Trans. 1 (1999):1827-1831.
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