1268853-39-9Relevant academic research and scientific papers
Enantioselective σ1 receptor binding and biotransformation of the spirocyclic PET tracer 1′-benzyl-3-(3-fluoropropyl)-3H-spiro[[2] benzofuran-1,4′-piperidine]
Wiese, Christian,Maestrup, Eva Grosse,Schepmann, Dirk,Grimme, Stefan,Humpf, Hans-Ulrich,Brust, Peter,Wuensch, Bernhard
experimental part, p. 148 - 154 (2011/11/05)
It was shown that racemic (±)-2 [1′-benzyl-3-(3-fluoropropyl)- 3H-spiro[[2]benzofuran-1,4′-piperidine], WMS-1813] represents a promising positron emission tomography (PET) tracer for the investigation of centrally located σ1 receptors. To study the pharmacological activity of the enantiomers of 2, a preparative HPLC separation of (R)-2 and (S)-2 was performed. The absolute configuration of the enantiomers was determined by CD-spectroscopy together with theoretical calculations of the CD-spectrum of a model compound. In receptor binding studies with the radioligand [ 3H]-(+)-pentazocine, (S)-2 was thrice more potent than its (R)-configured enantiomer (R)-2. The metabolic degradation of the more potent (S)-enantiomer was considerably slower than the metabolism of (R)-2. The structures of the main metabolites of both enantiomers were elucidated by determination of the exact mass using an Orbitrap-LC-MS system. These experiments showed a stereoselective biotransformation of the enantiomers of 2. Copyright
