The structure of McN-5652

The configuration of the diastereoisomers of 6-(4-methylthiophenyl)-1,2,3,5,6,10b-hexahydropyrrolo[2,1- a]isoquinoline 1 (McN-5652) is determined and unequivocally assigned by NMR spectroscopy (NOE measurements) and an X-ray structural analysis of the trans diastereoisomer. The enantiomers of cis- 1...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2001-08, Vol.9 (8), p.2105-2111
Main Authors: Schulze, Oliver, Schmidt, Ulrich, Voss, Jürgen, Nebeling, Bruno, Adiwidjaja, Gunadi, Scharwächter, Klaus
Format: Article
Language:English
Subjects:
Biological and medical sciences
Chromatography, High Pressure Liquid
Condensed matter: structure, mechanical and thermal properties
Crystallography, X-Ray
Exact sciences and technology
Heterocyclic compounds
Isoquinolines - chemistry
Magnetic Resonance Spectroscopy
Medical sciences
Molecular Conformation
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Organic compounds
Pharmacology. Drug treatments
Physics
Serotonin Antagonists - chemistry
Serotoninergic system
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
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Summary:The configuration of the diastereoisomers of 6-(4-methylthiophenyl)-1,2,3,5,6,10b-hexahydropyrrolo[2,1- a]isoquinoline 1 (McN-5652) is determined and unequivocally assigned by NMR spectroscopy (NOE measurements) and an X-ray structural analysis of the trans diastereoisomer. The enantiomers of cis- 1 are separated by preparative HPLC on a chiral phase. One of the enantiomers of cis- 1 represents the precursor for imaging the serotonin 5-HT transporter with positron emission tomography (PET). The configuration of the diastereisomers of McN-5652 1 is determined and unequivocally assigned by NMR spectroscopy (NOE measurements) and an X-ray structural analysis of the trans diastereomer.
ISSN:0968-0896
1464-3391
DOI:10.1016/S0968-0896(01)00117-1