Document Detail


Antimalarial activity of new water-soluble dihydroartemisinin derivatives. 2. Stereospecificity of the ether side chain.
MedLine Citation:
PMID:  2657065     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A new series of hydrolytically stable and water-soluble dihydroartemisinin derivatives with optically active side chains was prepared as potential antimalarial agents. This was an effort to prepare compounds with activity superior to that of artelinic acid and to examine the impact of the stereospecificity of the introduced alkyl side chain on biological properties. The ester derivatives (6a-d) possess superior in vitro activity to artemisinin, artemether, and arteether against two strains of Plasmodium falciparum (D-6 and W-2); however, conversion of the esters to their corresponding acids drastically reduces their antimalarial activity. None of the new acids possess in vitro antimalarial activity superior to that of artelinic acid. Although there appears to be limited stereospecificity for antimalarial activity among the acids (7a-d) tested, significant differences in antimalarial activity was seen among the esters.
Authors:
A J Lin; M Lee; D L Klayman
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Publication Detail:
Type:  Comparative Study; Journal Article    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  32     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  1989 Jun 
Date Detail:
Created Date:  1989-07-11     Completed Date:  1989-07-11     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1249-52     Citation Subset:  IM    
Affiliation:
Division of Experimental Therapeutics, Walter Reed Army Institute of Research, Washington, D.C. 20307-5100.
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MeSH Terms
Descriptor/Qualifier:
Animals
Artemisinins*
Chemical Phenomena
Chemistry
Malaria / drug therapy
Mice
Molecular Structure
Plasmodium falciparum / drug effects*
Sesquiterpenes / chemical synthesis,  pharmacology*,  therapeutic use
Solubility
Stereoisomerism
Structure-Activity Relationship
Water
Chemical
Reg. No./Substance:
0/Artemisinins; 0/Sesquiterpenes; 71939-50-9/dihydroquinghaosu; 7732-18-5/Water

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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