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Stereochemical studies of 3‐aryl‐3‐methylpiperidines of potential opioid ligand activities by high‐resolution 1 H and 13 C NMR spectroscopy
Author(s) -
Casy A. F.,
Iorio M. A.,
Madani A. E.
Publication year - 1987
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260250614
Subject(s) - chemistry , aryl , ligand (biochemistry) , stereochemistry , nuclear magnetic resonance spectroscopy , high resolution , two dimensional nuclear magnetic resonance spectroscopy , proton nmr , nmr spectra database , carbon 13 nmr , carbon 13 nmr satellite , spectral line , fluorine 19 nmr , organic chemistry , receptor , alkyl , biochemistry , physics , astronomy , remote sensing , geology
The 1 H (270, 400 MHz) and 13 C (22.5, 67.5 MHz) NMR spectra of a series of 2,3‐3,5‐ and 3,6‐dimethyl‐3‐( m ‐hydroxy‐ m ‐methoxy‐phenyl)piperidines of proven or potential opioid ligand activity are reported. The data were analysed in terms of configuration and preferred conformation, and some key deductions were confirmed by NOED and 2D COSY experiments. In the 3,5‐dimethyl derivatives, isomers with preferred axial or equatorial 3‐aryl substituents were identified.