Structure–Activity Relationships of Lactone Ring-Opened Analogs of the Antimalarial 1,2,4-Trioxane Artemisinin
1,2,4-Trioxane benzylic ethers 8a–e were prepared as simplified, tricyclic versions of the clinically used tetracyclic antimalarial drug artemisinin (1). Five additional artemisinin analogs (9–11) were prepared. Neither water solubility (analogs 8e and 11b) nor chelating ability (analogs 9 and 10),...
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th-mahidol.172442018-07-04T14:02:58Z Structure–Activity Relationships of Lactone Ring-Opened Analogs of the Antimalarial 1,2,4-Trioxane Artemisinin Gary H. Posner David J. McGarvey Chang Ho Oh Nirbhay Kumar Steven R. Meshnick Wanida Asawamahasadka Johns Hopkins University Inje University Johns Hopkins Bloomberg School of Public Health University of Michigan School of Public Health Mahidol University Biochemistry, Genetics and Molecular Biology Pharmacology, Toxicology and Pharmaceutics 1,2,4-Trioxane benzylic ethers 8a–e were prepared as simplified, tricyclic versions of the clinically used tetracyclic antimalarial drug artemisinin (1). Five additional artemisinin analogs (9–11) were prepared. Neither water solubility (analogs 8e and 11b) nor chelating ability (analogs 9 and 10), however, produced trioxanes of especially high in vitro antimalarial activity. Trioxane fluorobenzyl ether 8b is the most active in this series (more active than artemisinin) against Plasmodium falciparum parasites in vitro, with substantial activity also in mice infected with Plasmodium berghei parasites and with 10 times higher activity than artemisinin (1) in killing immature P. falciparum gametocytes. © 1995, American Chemical Society. All rights reserved. 2018-07-04T06:52:20Z 2018-07-04T06:52:20Z 1995-02-01 Article Journal of Medicinal Chemistry. Vol.38, No.4 (1995), 607-612 10.1021/jm00004a006 15204804 00222623 2-s2.0-0029061802 https://repository.li.mahidol.ac.th/handle/123456789/17244 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0029061802&origin=inward |
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Biochemistry, Genetics and Molecular Biology Pharmacology, Toxicology and Pharmaceutics Gary H. Posner David J. McGarvey Chang Ho Oh Nirbhay Kumar Steven R. Meshnick Wanida Asawamahasadka Structure–Activity Relationships of Lactone Ring-Opened Analogs of the Antimalarial 1,2,4-Trioxane Artemisinin |
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1,2,4-Trioxane benzylic ethers 8a–e were prepared as simplified, tricyclic versions of the clinically used tetracyclic antimalarial drug artemisinin (1). Five additional artemisinin analogs (9–11) were prepared. Neither water solubility (analogs 8e and 11b) nor chelating ability (analogs 9 and 10), however, produced trioxanes of especially high in vitro antimalarial activity. Trioxane fluorobenzyl ether 8b is the most active in this series (more active than artemisinin) against Plasmodium falciparum parasites in vitro, with substantial activity also in mice infected with Plasmodium berghei parasites and with 10 times higher activity than artemisinin (1) in killing immature P. falciparum gametocytes. © 1995, American Chemical Society. All rights reserved. |
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Johns Hopkins University |
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Johns Hopkins University Gary H. Posner David J. McGarvey Chang Ho Oh Nirbhay Kumar Steven R. Meshnick Wanida Asawamahasadka |
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Article |
author |
Gary H. Posner David J. McGarvey Chang Ho Oh Nirbhay Kumar Steven R. Meshnick Wanida Asawamahasadka |
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Gary H. Posner |
title |
Structure–Activity Relationships of Lactone Ring-Opened Analogs of the Antimalarial 1,2,4-Trioxane Artemisinin |
title_short |
Structure–Activity Relationships of Lactone Ring-Opened Analogs of the Antimalarial 1,2,4-Trioxane Artemisinin |
title_full |
Structure–Activity Relationships of Lactone Ring-Opened Analogs of the Antimalarial 1,2,4-Trioxane Artemisinin |
title_fullStr |
Structure–Activity Relationships of Lactone Ring-Opened Analogs of the Antimalarial 1,2,4-Trioxane Artemisinin |
title_full_unstemmed |
Structure–Activity Relationships of Lactone Ring-Opened Analogs of the Antimalarial 1,2,4-Trioxane Artemisinin |
title_sort |
structure–activity relationships of lactone ring-opened analogs of the antimalarial 1,2,4-trioxane artemisinin |
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2018 |
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https://repository.li.mahidol.ac.th/handle/123456789/17244 |
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1763490041012682752 |