Abstract:
:A number of novel pyridazinomorphinans have been synthesized by the inverse electron demand Diels-Alder reaction of various 3,6-disubstituted 1,2,4,5-tetrazines with enamines derived from dihydrocodeinone and with codeinone. Reduction of some of the pyridazinomorphinans did not furnish the expected pyrroloepoxymorphinans; in all cases investigated reductive cleavage of the epoxybridge was observed to yield dihydropyridazino- or pyrrolomorphinans. The structures of all new compounds were assigned by the spectral data, that of the cycloadduct of codeinone was additionally verified by X-ray crystallography. Compounds 5a, 8, 11a and 16 have been evaluated for their affinity at mu and kappa opioid receptors in radioligand binding assays. Their ability to inhibit [3H]DAMGO binding at mu and [3H]U 69.593 binding at kappa receptors, respectively as compared to codeine has been found to be lower.
journal_name
Arch Pharm (Weinheim)journal_title
Archiv der Pharmazieauthors
Klindert T,Stroetmann I,Seitz G,Höfner G,Wanner KT,Frenzen G,Eckhoff Bdoi
10.1002/ardp.19973300602subject
Has Abstractpub_date
1997-06-01 00:00:00pages
163-8issue
6eissn
0365-6233issn
1521-4184journal_volume
330pub_type
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