Synthesis and opioid activity of novel 6-substituted-6-demethoxy-ethenomorphinans

Barbara Czakó; János Marton; Sándor Berényi; Katarzyna Gach; Jakub Fichna; Martin Storr; Géza Tóth; Attila Sipos; Anna Janecka

doi:10.1016/j.bmc.2010.03.068

Synthesis and opioid activity of novel 6-substituted-6-demethoxy-ethenomorphinans

Bioorg Med Chem. 2010 May 15;18(10):3535-42. doi: 10.1016/j.bmc.2010.03.068. Epub 2010 Mar 29.

Authors

Barbara Czakó¹, János Marton, Sándor Berényi, Katarzyna Gach, Jakub Fichna, Martin Storr, Géza Tóth, Attila Sipos, Anna Janecka

Affiliation

¹ Department of Organic Chemistry, University of Debrecen, PO Box 20, H-4010, Debrecen, Hungary.

PMID: 20413312
DOI: 10.1016/j.bmc.2010.03.068

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Analgesics, Opioid / pharmacology*
Animals
Drug Design
Ileum / drug effects*
Ileum / physiology
Male
Mice
Molecular Structure
Muscle Contraction / drug effects*
Muscle, Smooth / drug effects*
Muscle, Smooth / physiology
Narcotic Antagonists / pharmacology*
Receptors, Opioid / agonists
Receptors, Opioid, mu / agonists

Substances

Analgesics, Opioid
Narcotic Antagonists
Receptors, Opioid
Receptors, Opioid, mu