Atropisomerism in the Vaptan Class of Vasopressin Receptor Ligands: The Active Conformation Recognized by the Receptor

Abstract

Latent chirality: Atropisomerism in the vaptan class of vasopressin receptor ligands with N-benzoyl benzo-fused seven-membered-ring nitrogen heterocycles was investigated by freezing the axis by ortho substitution. The aS/aR atropisomers caused by the ArN(CO) axis were separated to reveal that the vasopressin receptor recognizes the cis,aS conformation (see picture; R=CH3, X=CO, Y=H) when it binds to the ligand.