Kenneth F Bastow

UNCCH, Eshelman School of Pharmacy, Pharmacy

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Total synthesis and bioactivity of unique flavone desmosdumotin B and its analogs

Kyoko Nakagawa-Goto; Kenneth F. Bastow; Jiu-Hong Wu; Harukuni Tokuda; Kuo-Hsiung Lee (Profiled Authors: Kenneth F Bastow; Kuo-Hsiung Lee; Kyoko Nakagawa-Goto)

Bioorganic and Medicinal Chemistry Letters. 2005;15(12):3016-3019.

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 μg/mL compared to >40 μg/mL against the parental KB cell line. Flavone 7 displayed selective activity against 1A9 ovarian carcinoma with an ED50 value of 0.7 μg/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. © 2005 Elsevier Ltd. All rights reserved.

PMID: 15913998    

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