Rigid Multivalent Scaffolds Based on Adamantane

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• 作者：Khaled Nasr ; Nadine Pannier ; John V. Frangioni ; Wolfgang Maison
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：February 1, 2008
• 年：2008
• 卷：73
• 期：3
• 页码：1056 - 1060
• 全文大小：84K
• 年卷期：v.73,no.3(February 1, 2008)
• ISSN：1520-6904

文摘

We present two new synthetic strategies to rigid multivalent scaffolds of the general structure 1 based onadamantane. Both routes start from arylated adamantane derivatives and give the target compounds 12and 18 in 5 and 7 steps, respectively. These scaffolds have been designed for the assembly of multivalentbinders for cell surface epitopes. The adamantane nucleus exposes three carboxylic acid groups in awell-defined tripodal geometry for conjugation of targeting ligands. In addition, an amino group at thefourth bridgehead position provides a flexible linker for attachment of effector molecules such as contrastagents, radiotracers, or cytotoxins without interfering with the cell binding process.