Abstract
A targeted series of chalcone and dienone hybrid compounds containing aminoquinoline and nucleoside templates was synthesized and evaluated for in vitro antimalarial activity. The Cu(I)-catalyzed cycloaddition of azides and terminal alkynes was applied as the hybridization strategy. Several chalcone-chloroquinoline hybrid compounds were found to be notably active, with compound 8b the most active, exhibiting submicromolar IC(50) values against the D10, Dd2 and W2 strains of Plasmodium falciparum.
Copyright © 2010 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkynes / chemistry
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Aminoquinolines / chemistry
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Animals
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Antimalarials / chemical synthesis*
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Antimalarials / chemistry
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Antimalarials / pharmacology
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Azides / chemistry
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Catalysis
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Chalcone / chemistry*
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Chalcones / chemical synthesis*
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Chalcones / chemistry
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Chalcones / pharmacology
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Copper / chemistry
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Drug Design
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Hemin / metabolism
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Nucleosides / chemistry
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Plasmodium falciparum / drug effects
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Quinolines / chemical synthesis*
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Quinolines / chemistry
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Quinolines / pharmacology
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Structure-Activity Relationship
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Triazoles / chemistry*
Substances
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3-(4-(1-(7-chloroquinolin-4-yl)-1H-(1,2,3)triazol-4-ylmethoxy)-3-methoxyphenyl)-1-(2,4-dimethoxyphenyl)propenone
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Alkynes
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Aminoquinolines
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Antimalarials
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Azides
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Chalcones
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Nucleosides
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Quinolines
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Triazoles
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Chalcone
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Hemin
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Copper