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Title

Fentanyl and its analogue N-(1-phenylpyrazol-3-yl)-N-[1-(2-phenylethyl)-4-piperidyl]propanamide: H-1- and C-13-NMR spectroscopy, X-ray crystallography, and theoretical calculations

AuthorsJimeno, M. Luisa; Alkorta, Ibon ; Cano, Carolina; Jagerovic, Nadine ; Goya, Pilar ; Elguero, José ; Foces-Foces, Concepción
Keywordspyrazole
analgesia
fentanyl
crystal structure
GIAO
B3LYP
Issue Date2003
PublisherPharmaceutical Society of Japan
CitationChemical and Pharmaceutical Bulletin 51(8) : 929—934 (2003)
AbstractThe oxalate salts and free bases of fentanyl and N-[1-(2-phenylethyl)-4-piperidyl]-N-(1-phenyl-4- pyrazolyl)propanamide, a new lead compound for long-acting analgesia, have been characterized by 1H- and 13C- NMR spectroscopy. The crystal structure of the hydrochloride of N-[1-(2-phenylethyl)-4-piperidyl]-N-(1-phenyl- 4-pyrazolyl)propanamide monohydrate has been determined. Two centrosymmetrically related cations, joined through C(phenyl)-H…p contacts, encapsulate a large void that contains pairs of anions and bridged water molecules into a zero-dimensional (0D) supramolecular motif. The cations are linked to this framework via N1H…Cl contacts. GIAO/B3LYP calculations have been carried out to compare the experimental 13C chemical shifts with the absolute shieldings thus calculated. The protonation of both molecules takes place on the piperi- dine ring (axial protonation), as has been verified both in the solid state (X-ray) and in solution (NMR).
URIhttp://hdl.handle.net/10261/34984
ISSN0009-2363
Appears in Collections:(CENQUIOR) Artículos
(IQM) Artículos
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