Antitumor Agents. II : Regio- and Stereospecific Syntheses of 1-β-Alkyl-1-desoxypodophyllotoxin Derivatives and Biological Activity
スポンサーリンク
概要
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1-β-Alkyl derivatives of 1-desoxypodophyllotoxin were synthesized, and their cytotoxicity and inhibitory effects on DNA topoisomerase II (Topo-II) and tubulin polymerization were examined.The reaction of epipodophyllotoxin derivatives (1a-c) with trimethylallylsilane in the presence of boron trifluoride etherate gave 1-β-allylated compounds (2a-c). The regiochemistry and the β-stereochemistry of the 1-allyl group were confirmed by comparison of the ^<13>C-NMR spectra and NOE's (%) of 2c, podophyllotoxin (POD) and epipodophyllotoxin (1b). 1-β-Alkyl-1-desoxypodophyllotoxin derivatives (3-8) were prepared from 2b.None of the tested compounds (3-8) showed any inhibitory effect on Topo-II. 1-β-Propyl compound (3) and its 4'-demethyl compound (4) inhibited tubulin polymerization and the cytotoxicities of these compounds were equal to that of VP-16. 1-β-(2,3-Dihydroxypropyl) compounds (5 and 8) and 1-β-(2,3-diacetoxypropyl) compounds (6 and 7)showed no inhibitory effect on tubulin polymerization. Although 5 did not inhibit either Topo-II activity or tubulin polymerization, it showed a high cytotoxicity against sarcoma 180.
- 社団法人日本薬学会の論文
- 1993-05-15
著者
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吉田 健一郎
Tokushima Institute Taiho Pharmaceutical Co. Ltd.
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寺田 忠史
Hanno Research Center, Taiho Pharmaceutical Co., Ltd.,
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藤本 勝彦
Hanno Research Center, Taiho Pharmaceutical Co., Ltd.,
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野村 誠
Hanno Research Center, Taiho Pharmaceutical Co., Ltd.,
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山下 純一
Hanno Research Center, Taiho Pharmaceutical Co., Ltd.,
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WIERZBA Konstanty
Hanno Research Center, Taiho Pharmaceutical Co., Ltd.,
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小武内 尚
Tokushima Institute, Taiho Pharmaceutical Co., Ltd.,
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武田 節夫
Tokushima Institute, Taiho Pharmaceutical Co., Ltd.,
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南 慶典
Tokushima Institute, Taiho Pharmaceutical Co., Ltd.,
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山口 秀夫
Osaka University of Pharmaceutical Sciences
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山田 雄次
Hanno Research Center, Taiho Pharmaceutical Co., Ltd.
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藤本 勝彦
Hanno Research Center Taiho Pharmaceutical Co. Ltd.
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山下 純一
Hanno Research Center Taiho Pharmaceutical Co. Ltd.
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寺田 忠史
Hanno Research Center Taiho Pharmaceutical Co. Ltd.
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小武内 尚
Tokushima Institute Taiho Pharmaceutical Co. Ltd.
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Wierzba K
Taiho Pharmaceutical Co. Ltd. Saitama
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Wierzba Konstanty
Hanno Research Center Taiho Pharmaceutical Co. Ltd.
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Wierzba Konstanty
Taiho Pharmaceutical Co. Ltd. Hanno Research Center
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南 慶典
Tokushima Institute Taiho Pharmaceutical Co. Ltd.
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山田 雄次
Hanno Research Center Taiho Pharmaceutical Co. Ltd.
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野村 誠
Hanno Research Center Taiho Pharmaceutical Co. Ltd.
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武田 節夫
Tokushima Institute Taiho Pharmaceutical Co. Ltd.
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