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

Artigo Revisado por pares

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

2002; American Chemical Society; Volume: 45; Issue: 17 Linguagem: Inglês

10.1021/jm020133q

ISSN

1520-4804

Autores

Kazumi Kondo, Keizo Kan, Yoshihisa Tanada, Masahiko Bando, Tomoichi Shinohara, Muneaki Kurimura, Hidenori Ogawa, Shigeki Nakamura, Takahiro Hirano, Yoshitaka Yamamura, Masaru Kido, Toyoki Mori, Michiaki Tominaga,

Tópico(s)

Chemical Reaction Mechanisms

Resumo

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 (10) was determined by X-ray crystallographic analysis. After evaluation of both enantiomers (compounds R-2, S-2) for binding affinity, cAMP accumulation, and an in vivo study using Brattleboro rats, R-2 showed more potent activity as a V(2) receptor agonist than S-2.

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