Synthesis, structural, conformational and pharmacological study of new fentanyl derivatives of the camphidine system

Autor: Agustin Berisa, L. Labeaga, Enrique Gálvez, M.S. Arias, B. Rico, M. L. Izquierdo, A. Orjales
Rok vydání: 1994
Předmět:
Zdroj: Scopus-Elsevier
ISSN: 1943-5193
0022-152X
DOI: 10.1002/jhet.5570310209
Popis: A series of N-phenethyl-8-β-amidocamphidines (4a-f) (3-phenethyl-8-β- (N-arylamido)-3-azabicyclo[3.2.1]octane) has been designed, synthesized and stereochemically characterized as semirigid analogous of the 4-ani- lidopiperidine analgesics in an attempt to study the influence of cer- tain stereochemical factors on analgesia in this class of compounds. In deuteriochloroform and deuteriobenzene solution, compounds (4a-f) dis- play the same preferred conformation. The cyclopentane and piperidine rings adopt an envelope and distorted chair conformation respectively flattened at N-3, with the N and C-8 substituents in equatorial and ax- ial positions with respect to the piperidine ring. In vivo pharmacolo- gical testing demonstrated that compounds (4a-f) were inactive in the analgesic test, with the exception of compound (4f) which showed an ED 50 of 250 mg/kg p.o
Databáze: OpenAIRE
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