Medicinal and radiopharmaceutical chemistry with phenylazocarboxylic esters

• Applicants: Professor Dr. Markus Heinrich; Professor Dr. Olaf Prante
• Subject Area: Biological and Biomimetic Chemistry
• Term: from 2009 to 2019
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 104754872

Within our preliminary work we have been able to demonstrate that phenylazocarboxylic acid esters can be well suited reagents for nucleophilic aromatic substitutions and a wide range of further transformations. Based on our current results two fields of application in medicinal chemistry appear especially attractive, which we would now like to investigate in more detail. In the first subproject, phenylazocarboxylates shall be evaluated with regard to an application in combinatorial synthesis, which plays a key role in todays drug development. After a nucleophilic aromatic substitution as a first step, which is already known to be feasible under mild conditions and with high selectivity, diverse further transformations shall be conducted with the azocarbonyl unit as central reactive moiety. The aim hereby is to establish phenylazocarboxylates as highly versatile bifunctional reagents. The research planned within the second subproject is based on the key observation that phenylazocarboxylates can be radioactively labeled with [18F]fluoride ions in less than one minute and with high yields. The new methodologies developed in the first subproject shall then be used for the straightforward and efficient synthesis of new radioligands for PET studies.

• DFG Programme: Research Grants