Abstract
A novel enantioselective approach to the synthesis of a compound collection inspired by natural pyrrolizidine alkaloids was developed, employing an enantioselectively catalyzed 1,3-dipolar cycloaddition as the key step. The cycloadducts were obtained with excellent enantio- and diastereoselectivity. Biological evaluation of the resulting compound collection revealed that the compound class has multiple bioactivities, including activity against Plasmodium falciparum 3D7 and inhibition of Hedgehog signaling.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antimalarials / chemical synthesis*
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Antimalarials / pharmacology*
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Biological Products / chemistry
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Catalysis
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Cell Line
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Cycloaddition Reaction
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Hedgehog Proteins / metabolism
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Mice
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Mice, Inbred C3H
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Plasmodium falciparum / drug effects
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Plasmodium falciparum / growth & development
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Pyrrolizidine Alkaloids / chemical synthesis*
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Pyrrolizidine Alkaloids / pharmacology*
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Stereoisomerism
Substances
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Antimalarials
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Biological Products
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Hedgehog Proteins
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Pyrrolizidine Alkaloids