- Unified Total Synthesis of Five Bufadienolides
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We report a unified total synthesis of five bufadienolides: bufalin (1), bufogenin B (2), bufotalin (3), vulgarobufotoxin (4), and 3-(N-succinyl argininyl) bufotalin (5). After the steroidal ABCD ring 8 was produced, the D ring was cross-coupled with a 2-pyrone moiety and stereoselectively epoxidized to generate 6. TMSOTf promoted a stereospecific 1,2-hydride shift from 6 to establish the β-oriented 2-pyrone of 19. Functional group manipulations from 19 furnished 1-5, which potently inhibited cancer cell growth.
- Hagiwara, Koichi,Inoue, Masayuki,Itoh, Hiroaki,Shimizu, Shinsuke
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- Studies on cytotoxic constituents from the skin of the toad Bufo bufo gargarizans
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To study the chemical composition of the skin of Bufo bufo gargarizans, many kinds of chromatography methods were used in the isolation procedures, while the structures of isolated compounds were determined on the basis of their NMR and MS spectral analysis. As a result, two new compounds were isolated from its ethanolic extract and characterized as cinobufotalin 3-nonanedioylarginine ester (8) and bufotalin 3-pimeloylarginine ester (14). Furthermore, 13 known compounds were obtained. Isolated bufadienolides showed significant inhibition effect against SMMC-7721 cell lines in vitro.
- Zhao, Hu-Yi,Wu, Fu-Kai,Qiu, Ying-Kun,Wu, Zhen,Jiang, Yong-Tao,Chen, Ji-Yong
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experimental part
p. 793 - 800
(2010/12/20)
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