Abstract
Protoapigenone (1), isolated from Thelypteris torresiana, previously showed significant cytotoxic activity against five human cancer cell lines. In a continued structure-activity relationship study, the first total synthesis and modification of 1 were achieved. All synthesized compounds and related intermediates were evaluated for cytotoxic activity against five human cancer cell lines, HepG2, Hep3B, MDA-MB-231, MCF-7, and A549. Among them, 24 showed 2.2-14.2-fold greater cytotoxicity than 1 and naphthyl A-ring analogues remarkably enhanced the activity.
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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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology
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Cell Line, Tumor
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Cyclohexanones / chemical synthesis*
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Cyclohexanones / chemistry
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Cyclohexanones / pharmacology
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Drug Screening Assays, Antitumor
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Flavones / chemical synthesis*
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Flavones / chemistry
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Flavones / pharmacology
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Flavonoids / chemical synthesis*
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Flavonoids / chemistry
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Flavonoids / pharmacology
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Humans
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Structure-Activity Relationship
Substances
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5-hydroxy-2-(1-hydroxy-4-oxocyclohexa-2,5-dienyl)-7-methoxy-4H-chromen-4-one
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Antineoplastic Agents
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Cyclohexanones
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Flavones
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Flavonoids
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protoapigenone