Total Synthesis of Isoprekinamycin: Structural Evidence for Enhanced Diazonium Ion Character and Growth Inhibitory Activity toward Cancer Cells

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• 作者：Wei Liu ; Matthew Buck ; Nan Chen ; Muhong Shang ; Nicholas J. Taylor ; Jalil Asoud ; Xing Wu ; Brian B. Hasinoff ; Gary I. Dmitrienko
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：July 19, 2007
• 年：2007
• 卷：9
• 期：15
• 页码：2915 - 2918
• 全文大小：210K
• 年卷期：v.9,no.15(July 19, 2007)
• ISSN：1523-7052

文摘

The structurally novel diazobenzo[a]fluorene antibiotic isoprekinamycin (IPK) has been synthesized for the first time employing a Suzukicoupling of a brominated AB ring synthon with a boronate ester representing the D ring, followed by anionic cyclization and appropriatefunctional group manipulations. The first indication that the diazobenzo[a]fluorene system exhibits in vitro anticancer activity is provided andX-ray crystallographic evidence for enhancement of diazonium ion character as a consequence of intramolecular H-bonding is described.