Abstract
The structure of the natural dipyranocoumarin dipetalolactone has been confirmed by an unambiguous synthetic route from resorcinol. This sequence was initiated by a pyran ring formation step which introduced the 3-chloro-3-methylbut-1-yne moiety. Then, the expected product undergoes a Fremy's salt-meditated oxidative addition followed by ring closure to yield dipetalolactone. Dipetalolactone was also found to have immunological activity in a mouse carcinoma S180-bearing mice cell line.
MeSH terms
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Acetylation
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Animals
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / pharmacology
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Cell Line, Tumor
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Chromones / chemical synthesis*
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Chromones / pharmacology
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Cytotoxicity, Immunologic / drug effects
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Drug Screening Assays, Antitumor
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Female
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Immunologic Factors / chemical synthesis*
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Immunologic Factors / pharmacology
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Killer Cells, Natural / drug effects
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Killer Cells, Natural / immunology
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Lethal Dose 50
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Male
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Mice
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Mice, Inbred ICR
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Neoplasm Transplantation
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Nitroso Compounds / chemistry*
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Oxidation-Reduction
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Tumor Burden / drug effects
Substances
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Antineoplastic Agents
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Chromones
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Immunologic Factors
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Nitroso Compounds
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dipetalolactone
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Fremy's salt