Design and synthesis of thienylpyridyl garlands as non-peptidic alpha helix mimetics and potential protein–protein interactions disruptors

Abstract This paper describes an efficient route leading to new thienylpyridyl garlands as non-peptidic alpha helix mimetics and potential protein–protein interactions disruptors. Firstly, we have studied the reactivity of boronic acids and halogenated pyridines and/or thiophenes towards the Suzuki–Miyaura cross-coupling reaction in order to obtain bis-thienylpyridines. Secondly, we have functionalized these compounds by a reaction of bromination and the resultant bis-bromothienylpyridines have been found to undergo iterative Pd-catalyzed coupling based on a pseudo-Garlanding approach with a range of pyridyl boronic acids to produce a new library of thienylpyridyl oligomers.