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Synthesis, structural, conformational and pharmacological study of new fentanyl derivatives of the camphidine system
Author(s) -
Rico B.,
Gálvez E.,
Izquierdo M. L.,
Arias M. S.,
Orjales A.,
Berisa A.,
Labeaga L.
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310209
Subject(s) - chemistry , fentanyl , stereochemistry , pharmacology , combinatorial chemistry , medicine
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‐anilidopiperidine analgesics in an attempt to study the influence of certain stereochemical factors on analgesia in this class of compounds. In deuteriochloroform and deuteriobenzene solution, compounds 4a‐f display 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 axial positions with respect to the piperidine ring. In vivo pharmacological 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.