Abstract
Rocaglamides are bioactive natural compounds which have a cyclopenta[b]benzofuran core structure. The total synthesis of a reported natural product, 3'-hydroxymethylrocaglate (5), was achieved using [3 + 2] cycloaddition between 3-hydroxyflavone and methyl cinnamate. We also describe the synthesis of rocaglamide heterocycle derivatives and evaluate their Wnt signal inhibitory activities. Compounds 4, 5, 22a, 22b, 22c and 23c showed potent Wnt signal inhibitory activity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Benzofurans / chemical synthesis
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Benzofurans / chemistry*
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Benzofurans / pharmacology*
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Biological Products / chemical synthesis
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Biological Products / chemistry
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Biological Products / pharmacology
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Cinnamates / chemical synthesis
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Cinnamates / chemistry
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Crystallography, X-Ray
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Cycloaddition Reaction
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Flavonoids / chemical synthesis
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Flavonoids / chemistry
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HEK293 Cells
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Humans
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Models, Molecular
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Wnt Proteins / antagonists & inhibitors*
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Wnt Proteins / metabolism
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Wnt Signaling Pathway / drug effects*
Substances
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3'-hydroxymethylrocaglate
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Benzofurans
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Biological Products
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Cinnamates
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Flavonoids
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Wnt Proteins
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cinnamic acid
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rocaglamide
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3-hydroxyflavone