Crystal structure, absolute configuration, and phosphodiesterase inhibitory activity of (+)-1-(4-bromobenzyl)-4-[(3-cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone
| Autor: | Paul W. Baures, L. B. Cieslinski, Karl F. Erhard, Siegfried B. Christensen, Drake S. Eggleston, Theodore J. Torphy |
|---|---|
| Rok vydání: | 1993 |
| Předmět: |
Phosphodiesterase Inhibitors
Stereochemistry Molecular Conformation Absolute configuration Phosphodiesterase Muscle Smooth Stereoisomerism Context (language use) Crystallography X-Ray Pyrrolidinones Chiral column chromatography chemistry.chemical_compound chemistry 3' 5'-Cyclic-AMP Phosphodiesterases Benzyl Compounds Drug Discovery Lactam Animals Molecular Medicine Cattle Enantiomer Rolipram Derivative (chemistry) |
| Zdroj: | Journal of Medicinal Chemistry. 36:3274-3277 |
| ISSN: | 1520-4804 0022-2623 |
| DOI: | 10.1021/jm00074a007 |
| Popis: | Chiral HPLC resolution of the phosphodiesterase IV (PDE IV) inhibitor rolipram (1) provided (-)-1, and this enantiomer was converted into its 1-(4-bromobenzyl) derivative, (+)-2. X-ray structural analysis of (+)-2 established the absolute configuration as R, which provides the first direct evidence for a previously assumed assignment of configuration. The crystal structure of (+)-2 and the PDE inhibitory activity of both enantiomers of 2 are discussed in the context of a previously proposed topological model. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|