title: Synthesis of fused bicyclic piperidines: potential bioactive templates for medicinal chemistry.
abstract: 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.
authors.affiliation: Department of Chemistry, Vertex Pharmaceuticals, Inc., 11010 Torreyana Road, San Diego, California 92121, United States.
authors.forename: Jinglan
authors.initials: J
authors.lastname: Zhou
authors.affiliation: Department of Chemistry, Vertex Pharmaceuticals, Inc., 11010 Torreyana Road, San Diego, California 92121, United States.
authors.forename: Erica L
authors.initials: EL
authors.lastname: Campbell-Conroy
authors.affiliation: Department of Chemistry, Vertex Pharmaceuticals, Inc., 11010 Torreyana Road, San Diego, California 92121, United States.
authors.forename: Alina
authors.initials: A
authors.lastname: Silina
authors.affiliation: Department of Chemistry, Vertex Pharmaceuticals, Inc., 11010 Torreyana Road, San Diego, California 92121, United States.
authors.forename: Johnny
authors.initials: J
authors.lastname: Uy
authors.affiliation: Department of Chemistry, Vertex Pharmaceuticals, Inc., 11010 Torreyana Road, San Diego, California 92121, United States.
authors.forename: Fabrice
authors.initials: F
authors.lastname: Pierre
authors.affiliation: Department of Chemistry, Vertex Pharmaceuticals, Inc., 11010 Torreyana Road, San Diego, California 92121, United States.
authors.forename: Dennis J
authors.initials: DJ
authors.lastname: Hurley
authors.affiliation: Department of Chemistry, Vertex Pharmaceuticals, Inc., 11010 Torreyana Road, San Diego, California 92121, United States.
authors.forename: Nicole
authors.initials: N
authors.lastname: Hilgraf
authors.affiliation: Department of Chemistry, Vertex Pharmaceuticals, Inc., 11010 Torreyana Road, San Diego, California 92121, United States.
authors.forename: Bryan A
authors.initials: BA
authors.lastname: Frieman
authors.affiliation: Department of Chemistry, Vertex Pharmaceuticals, Inc., 11010 Torreyana Road, San Diego, California 92121, United States.
authors.forename: Michael P
authors.initials: MP
authors.lastname: DeNinno
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002626:Chemistry, Pharmaceutical; D008968:Molecular Conformation; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D010880:Piperidines