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An array of six pyridyl-substituted fused bicyclic piperidines was prepared as novel cores for medicinal chemistry. For maximum diversity, the size of the fused ring varied from three to six atoms and contained up to two oxygen atoms. The pyridine ring was incorporated to improve physicochemical properties and to challenge the robustness of the chemistry. The presence of the pyridine did interfere with our initial approaches to these molecules, and in several instances, a blocking strategy had to be employed. These new scaffolds possess high sp3 character and may prove useful in multiple medicinal chemistry applications.

Citation

Jinglan Zhou, Erica L Campbell-Conroy, Alina Silina, Johnny Uy, Fabrice Pierre, Dennis J Hurley, Nicole Hilgraf, Bryan A Frieman, Michael P DeNinno. Synthesis of fused bicyclic piperidines: potential bioactive templates for medicinal chemistry. The Journal of organic chemistry. 2015 Jan 2;80(1):70-9

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PMID: 25405702

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