Rigid Multivalent Scaffolds Based on Adamantane

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.

Reactivities of the Prism‐Shaped Diamondoids [1(2)3]Tetramantane and [12312]Hexamantane (Cyclohexamantane)

“…Building multiple attachment points on the surface of diamondoids may be useful for manufacturing diamond nanowires, [47] cell surface binders, [48] or for the construction of strong self-assembled monolayers on gold surfaces. [49,50] Recently we prepared several disubstituted triamantanes and [121]tetramantanes and demonstrated that, although kinetically controlled disubstitutions lead to complicated mixtures of isomers, thermodynamically controlled transformations are rather selective.…”

Synthesis of azolyl-substituted derivatives of 1-adamantanecarboxylic acid

“…Adamantane, being the simplest and the most readily available of them attracts attention for its rigidity, relatively low molecular volume and lipophilicity [2][3][4]. Functionalized adamantanes find use in pharmaceutical applications [5][6][7], polymer synthesis [8], design of nanostructured materials [9,10], ionic liquids [11] and coordination chemistry [12,13].…”

Transition metal complexes with cage-opened diamondoid tetracyclo[7.3.1.14,12.02,7]tetradeca-6.11-diene

“…Additional benefits arise from the rigidity of the diamondoid cages allowing construction of various three-dimensional structures with well-defined and predictable topologies [5][6][7][8][9][10][11][12][13].…”

“…](PF 6 ) 2[28] by applying the same experimental conditions as for the related complex [Cu(bipy)(COD)]PF6 …”