Synthesis and Opioid Activity of Novel 6-ketolevorphanol Derivatives

Zsuzsanna      Gyulai; Antal      Udvardy; Attila      Cs. Bényei; Jakub      Fichna; Katarzyna      Gach; Martin      Storr; Géza      Tóth; Sándor      Antus; Sándor      Berényi; Anna      Janecka; Attila      Siposa

doi:10.2174/1573406411309010001

Abstract

Novel 6-ketolevorphanol analogs with diverse substitution patterns at ring C were synthesized and their binding affinities at the µ, δ and κ 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 Δ7,8 bond had no significant potency at any of the opioid receptor types. In contrast, analogs with the saturated ring C were either potent agonist or antagonist depending on the absence or presence of the hydroxyl group in position 14.

Keywords: Analgesics, Opioid receptors, Binding Assay, Agonist, Antagonist

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Medicinal Chemistry

Title:Synthesis and Opioid Activity of Novel 6-ketolevorphanol Derivatives

Volume: 9 Issue: 1

Author(s): Zsuzsanna Gyulai, Antal Udvardy, Attila Cs. Bényei, Jakub Fichna, Katarzyna Gach, Martin Storr, Géza Tóth, Sándor Antus, Sándor Berényi, Anna Janecka and Attila Siposa

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Keywords: Analgesics, Opioid receptors, Binding Assay, Agonist, Antagonist

Abstract: Novel 6-ketolevorphanol analogs with diverse substitution patterns at ring C were synthesized and their binding affinities at the µ, δ and κ 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 Δ7,8 bond had no significant potency at any of the opioid receptor types. In contrast, analogs with the saturated ring C were either potent agonist or antagonist depending on the absence or presence of the hydroxyl group in position 14.

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Gyulai Zsuzsanna, Udvardy Antal, Cs. Bényei Attila, Fichna Jakub, Gach Katarzyna, Storr Martin, Tóth Géza, Antus Sándor, Berényi Sándor, Janecka Anna and Siposa Attila, Synthesis and Opioid Activity of Novel 6-ketolevorphanol Derivatives, Medicinal Chemistry 2013; 9 (1) . https://dx.doi.org/10.2174/1573406411309010001