Synthesis and opioid activity of novel 6-substituted-6-demethoxy-ethenomorphinans.
A set of novel 6-substituted orvinols was synthesized and pharmacologically characterized in order to explore the effect of the polarity and steric effects of these new moieties on the opioid activity. It was revealed that longer 6-O-alkyl chains led to increased agonistic activities, while the lack of C6-etheral oxygen gave rise to an antagonistic profile at the opioid receptors in the mouse ileum.
Czakó
Barbara
B
Department of Organic Chemistry, University of Debrecen, PO Box 20, H-4010, Debrecen, Hungary.
Marton
János
J
Berényi
Sándor
S
Gach
Katarzyna
K
Fichna
Jakub
J
Storr
Martin
M
Tóth
Géza
G
Sipos
Attila
A
Janecka
Anna
A
D000701:Analgesics, Opioid / Q000494:pharmacology*; D000818:Animals; D015195:Drug Design; D007082:Ileum / Q000187:drug effects* / Q000502:physiology; D008297:Male; D051379:Mice; D015394:Molecular Structure; D009119:Muscle Contraction / Q000187:drug effects*; D009130:Muscle, Smooth / Q000187:drug effects* / Q000502:physiology; D009292:Narcotic Antagonists / Q000494:pharmacology*; D011957:Receptors, Opioid / Q000819:agonists; D017450:Receptors, Opioid, mu / Q000819:agonists
D000701:Analgesics, Opioid; D009292:Narcotic Antagonists; D011957:Receptors, Opioid; D017450:Receptors, Opioid, mu