Flexible synthetic access to a novel biarylic GC binding motif is presented, consisting of a pyridone connected to a fused pyrrolo[2,3- b]pyridone. Extensive molecular modeling led to an optimized design… Click to show full abstract
Flexible synthetic access to a novel biarylic GC binding motif is presented, consisting of a pyridone connected to a fused pyrrolo[2,3- b]pyridone. Extensive molecular modeling led to an optimized design with perfect complementarity to the Hoogsteen site inside DNA's major groove. A wide range of functional elements can be introduced by minor modifications of the synthetic strategy. Our approach relies on mild Pd-catalyzed coupling reactions, featuring a triple heterohalogenated orthogonally addressable pyridine as a key intermediate.
               
Click one of the above tabs to view related content.