Characterization of Orally Active Nonpeptide Vasopressin V<INF>2</INF> Receptor Agonist. Synthesis and Biological Evaluation of Both the (5R)- and (5S)-Enantioisomers of 2-[1-(2-Chloro-4-pyrrolidin-1-yl-benzoyl)-2,3,4,5-tetrahydro-1H-1-benzazepin- 5-yl]-N-isopropylacetamide

The synthesis and evaluation of both the (R)- and (S)-enantioisomers about the 5-position on a tetrahydro-1H-1-benzazepine derivative were described. The absolute configuration of the (R,R)-isomer (<BO>10</BO>) was determined by X-ray crystallographic analysis. After evaluation of both enantiomers (compounds R-<BO>2</BO>, S-<BO>2</BO>) for binding affinity, cAMP accumulation, and an in vivo study using Brattleboro rats, R-<BO>2</BO> showed more potent activity as a V<INF>2</INF> receptor agonist than S-<BO>2</BO>.