Rigid multivalent scaffolds based on adamantane

The Journal of Organic Chemistry
Khaled NasrWolfgang Maison

Abstract

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

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Citations

Jun 4, 2014·Biomaterials·Giuseppe LamannaAlberto Bianco
Dec 3, 2014·Journal of Peptide Science : an Official Publication of the European Peptide Society·Maxime Grillaud, Alberto Bianco
Feb 21, 2009·Chemistry : a European Journal·Andrey A FokinPeter R Schreiner
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Jul 1, 2015·Beilstein Journal of Organic Chemistry·Franziska KlitscheWolfgang Maison
Dec 29, 2020·Bioorganic Chemistry·Jan HajduchJiří Jiráček
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Jun 6, 2015·Bioconjugate Chemistry·Julie RussierAlberto Bianco
Oct 18, 2019·Journal of the American Chemical Society·Eva Magdalena EstiradoLuc Brunsveld
Dec 21, 2013·Journal of the American Chemical Society·Maxime GrillaudAlberto Bianco
Jun 10, 2014·The Journal of Organic Chemistry·Artem N SemakinVladimir A Tartakovsky
Oct 16, 2021·Organic & Biomolecular Chemistry·William K WeigelDavid B C Martin

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