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First total synthesis of protoapigenone and its analogues as potent cytotoxic agents.

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.

SUBMITTER: Lin AS

PROVIDER: S-EPMC2587018 | biostudies-literature | 2007 Aug

REPOSITORIES: biostudies-literature

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First total synthesis of protoapigenone and its analogues as potent cytotoxic agents.

Lin An-Shen AS Nakagawa-Goto Kyoko K Chang Fang-Rong FR Yu Donglei D Morris-Natschke Susan L SL Wu Chin-Chung CC Chen Shu-Li SL Wu Yang-Chang YC Lee Kuo-Hsiung KH

Journal of medicinal chemistry 20070710 16

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 ...[more]

PMID: 17622129

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