Preparation and Characterization of a New Artemisinin-Derived DimerClick to copy article linkArticle link copied!
Abstract
A new dimer (1) that is likely to be a reduction metabolite of arteether (2), the potent antimalarial agent, was prepared from deoxydihydroartemisinin (3). The identity of 1 was established from spectral data and was confirmed by X-ray crystallographic analysis. In addition, the stereochemistry of the related, previously reported dimer (4), is now more clearly defined, based on revising its X-ray crystallographic data.
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Abstract published in Advance ACS Abstracts, August 1, 1996.
Cited By
This article is cited by 17 publications.
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- Mankil Jung,, Sangmin Lee,, Jungyeob Ham,, Kyunghoon Lee,, Hanjo Kim, and, Soo Kie Kim. Antitumor Activity of Novel Deoxoartemisinin Monomers, Dimers, and Trimer. Journal of Medicinal Chemistry 2003, 46
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- Gary H. Posner,, Ik-Hyeon Paik,, Surojit Sur,, Andrew J. McRiner,, Kristina Borstnik,, Suji Xie, and, Theresa A. Shapiro. Orally Active, Antimalarial, Anticancer, Artemisinin-Derived Trioxane Dimers with High Stability and Efficacy. Journal of Medicinal Chemistry 2003, 46
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- Ahmed M. Galal,, Samir A. Ross,, Mahmoud A. ElSohly,, Hala N. ElSohly,, Farouk S. El-Feraly,, Mohamed S. Ahmed, and, Andrew T. McPhail. Deoxyartemisinin Derivatives from Photooxygenation of Anhydrodeoxydihydroartemisinin and Their Cytotoxic Evaluation. Journal of Natural Products 2002, 65
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- Sanchai Ekthawatchai,, Sumalee Kamchonwongpaisan,, Palangpon Kongsaeree,, Bongkoch Tarnchompoo,, Yodhathai Thebtaranonth, and, Yongyuth Yuthavong. C-16 Artemisinin Derivatives and Their Antimalarial and Cytotoxic Activities: Syntheses of Artemisinin Monomers, Dimers, Trimers, and Tetramers by Nucleophilic Additions to Artemisitene. Journal of Medicinal Chemistry 2001, 44
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- Aäron C. Beekman,, Adriaan R. W. Barentsen,, Herman J. Woerdenbag,, Wim Van Uden, and, Niesko Pras, , Antonius W. T. Konings, , Farouk S. El-Feraly and, Ahmed M. Galal, , Håkan V. Wikström. Stereochemistry-Dependent Cytotoxicity of Some Artemisinin Derivatives. Journal of Natural Products 1997, 60
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- Xiaosu Zou, Chang Liu, Congcong Li, Rong Fu, Wei Xu, Hongzhu Bian, Xun Dong, Xiaozhen Zhao, Zhenye Xu, Jinghua Zhang, Zhengwu Shen. Study on the structure-activity relationship of dihydroartemisinin derivatives: Discovery, synthesis, and biological evaluation of dihydroartemisinin-bile acid conjugates as potential anticancer agents. European Journal of Medicinal Chemistry 2021, 225 , 113754. https://doi.org/10.1016/j.ejmech.2021.113754
- Li Ying. Artemisinin Derivatives and Analogues. 2018, 177-196. https://doi.org/10.1016/B978-0-12-813133-6.00004-4
- Neesha Yadav, Chiranjeev Sharma, Satish Kumar Awasthi. Diversification in the synthesis of antimalarial trioxane and tetraoxane analogs. RSC Advances 2014, 4
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- Asish K. Bhattacharya, Ashish K. Pathak, Ram P. Sharma. Semi-synthesis of deoxyartemisinin. Mendeleev Communications 2007, 17
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- Poonsakdi Ploypradith. Development of artemisinin and its structurally simplified trioxane derivatives as antimalarial drugs. Acta Tropica 2004, 89
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- Gary H Posner, John Northrop, Ik-Hyeon Paik, Kristina Borstnik, Patrick Dolan, Thomas W Kensler, Suji Xie, Theresa A Shapiro. New chemical and biological aspects of artemisinin-Derived trioxane dimers. Bioorganic & Medicinal Chemistry 2002, 10
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- Ram P. Sharma, Asish K. Bhattacharya. Recent Developments on the Chemistry and Biological Activity of Artemisinin and Related Antimalarials — An Update. HETEROCYCLES 1999, 51
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- Braulio M. Fraga. Natural sesquiterpenoids. Natural Product Reports 1998, 15
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- Gary H. Posner, Poonsakdi Ploypradith, Whitney Hapangama, Dasong Wang, Jared N. Cumming, Patrick Dolan, Thomas W. Kensler, Donna Klinedinst, Theresa A. Shapiro, Qun Yi Zheng, Christopher K. Murray, Lynn G. Pilkington, Lalith R. Jayasinghe, Jeff F. Bray, Randy Daughenbaugh. Trioxane dimers have potent antimalarial, antiproliferative and antitumor activities in vitro. Bioorganic & Medicinal Chemistry 1997, 5
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