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The development of a modular synthesis of teraryl-based alpha-helix mimetics as potential inhibitors of protein-protein interactions

: Trobe, M.; Peters, M.; Grimm, S.H.; Breinbauer, R.


Synlett 25 (2014), Nr.9, S.1202-1214
ISSN: 0936-5214
ISSN: 1437-2096
Fraunhofer ICT ()

In this account we describe the evolution of our successful efforts to develop a modular synthesis of teraryl-based -helix mimetics as potential inhibitors of protein-protein interactions. At the center of our convergent synthetic route are 2-substituted 4-iodophenyl triflates as core fragments, which by consecutive Suzuki couplings with 5-substituted pyridin-3-ylboronic acids are converted into the desired teraryl compounds. With our strategy it should be possible to synthesize all 5670 variants of the teraryl -helix mimetics using a set of 2 × 18 building blocks featuring the side chains of the 18 proteinogenic amino acids that are of relevance for protein-protein interactions. 1 Introduction and Concept 1.1 Protein-Protein Interactions 1.2 -Helix Mimetics 1.3 Linear Synthesis of -Helix Mimetics 2 Modular Synthetic Route to Teraryls 2.1 Core Fragments 2.2 Pyridinylboronic Acids 3 Conclusion and Outlook.