Synthesis and absolute configuration of optically pure enantiomers of a ϰ‐opioid receptor selective agonist

FEBS Letters

George, Clifford³  Rice, Kenner C.¹  DeCosta, Brian¹  Rothman, Richard B.²  Jacobson, Arthur E.¹ 

[1] Section on Drug Design and Synthesis, Laboratory of Neuroscience, National Institute of Diabetes, Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892 USA;Laboratory of Clinical Science, National Institute of Mental Health, Bethesda, MD 20892 USA;Naval Research Laboratory, Washington, DC 20375, USA

关键词: X-ray analysis;    U50;    488 synthesis;    Absolute configuration;    (+)-trans-2-Pyrrolidinyl-N-methylcyclohexylamine;    ϰ-Opioid receptor agonist;    U50;    488;    (±)-trans-3;    4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)-cyclohexyl-1] benzene-acetamide;   

DOI  :  10.1016/0014-5793(87)80315-0

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

The enantiomers of U50,488 (1, in fig. 1), ligands highly selective for ϰ-opioid receptors, have been prepared by a refined procedure and their optical purity demonstrated. The absolute configuration of (+)-trans-2-pyrrolidinyl-N-methylcyclohexylamine, a chemically versatile intermediate for synthesis of analogs of ϰ-opioid receptor ligands with defined chirality, has been determined to be 1S,2S by X-ray crystallographic analysis. This intermediate has been used to synthesize the optically pure U50,488 enantiomers with known absolute configuration.

【 授权许可】

Unknown