Abstract
The first total synthesis of a unique flavone natural product, desmosdumotin B (1), was accomplished. Furthermore, three novel flavonoids, 6-8, and a novel chalcone, 9, were synthesized. The new compounds were evaluated as in vitro inhibitors of human cancer cell growth. The synthetic 1 showed significant cytotoxic activity against a multi-drug resistant cell line (KB-VIN) with an ED50 value of 2.0 microg/mL compared to >40 microg/mL against the parental KB cell line. Flavone 7 displayed selective activity against 1A9 ovarian carcinoma with an ED50 value of 0.7 microg/mL. Selected 1-analogs and synthetic intermediates were also screened for antitumor-promoting effects as inhibitors of EBV-EA activation. Among them, trihydroxyacetophenone derivatives 11 and 14 showed good activity.
Publication types
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Comparative Study
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alkenes / chemistry
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Alkenes / pharmacology
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Antigens, Viral / chemistry*
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Antigens, Viral / metabolism
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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 Proliferation / drug effects*
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Drug Resistance, Multiple
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Drug Resistance, Neoplasm
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Drug Screening Assays, Antitumor
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Flavones
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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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Ketones / chemistry
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Ketones / pharmacology
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Neoplasms / drug therapy
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Structure-Activity Relationship
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Tumor Cells, Cultured
Substances
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Alkenes
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Antigens, Viral
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Antineoplastic Agents
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Epstein-Barr virus early antigen
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Flavones
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Flavonoids
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Ketones
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desmosdumotin C
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flavone