Synthesis and Opioid Activity of Novel 6-ketolevorphanol Derivatives

Gyulai, Zsuzsanna and Udvardy, Antal and Bényei, Attila Csaba and Fichna, Jakub and Gach, Katarzyna and Storr, Martin and Tóth, Géza and Antus, Sándor and Berényi, Sándor and Sipos, Attila (2013) Synthesis and Opioid Activity of Novel 6-ketolevorphanol Derivatives. MEDICINAL CHEMISTRY, 9 (1). pp. 1-10. ISSN 1573-4064

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Abstract

Novel 6-ketolevorphanol analogs with diverse substitution patterns at ring C were synthesized and their binding affinities at the mu, delta and kappa opioid receptors were investigated. The in vitro activity of the new analogs was then evaluated in the functional assay based on the electrically-stimulated contractions of the mouse ileum. It was shown that analogs with Delta(7,8) bond had no significant potency at any of the opioid receptor types. In contrast, analogs with the saturated ring C were either potent kappa agonist or antagonist depending on the absence or presence of the hydroxyl group in position 14.

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