A small library of 3-thia-7,9-diazabicyclo[3.3.1]nonanes was synthesized and their opioid receptors affinity and selectivity evaluated. Among these novel sulfur-bridged compounds, the (E) 9-[3’-(3- chlorophenyl)-but-2’-en-1’-yl]-7-propionyl-3-thia-7,9-diazabicyclo[3.3.1]nonane 2i emerged as the derivative with the highest μ receptor affinity (Ki = 85 nM) and selectivity (Ki μ/δ = 58.8, Ki μ/κ > 117.6). The antinociceptive activity of 2i was also evaluated in acute thermal pain. Docking studies disclosed the specific pattern of interactions of these derivatives.
Synthesis, biological evaluation and docking studies of a novel class of sulfur-bridged diazabicyclo[3.3.1]nonanes / Murineddu, Gabriele; Asproni, Battistina; Corona, Paola; Gessi, Stefania; Merighi, Stefania; Battistello, Enrica; Sturaro, Chiara; Calò, Girolamo; Galeotti, Nicoletta; Temml, Veronika; Herdlinger, Sonja; Schuster, Daniela; Pinna, Gerard A.. - In: BIOORGANIC CHEMISTRY. - ISSN 0045-2068. - STAMPA. - (2020), pp. 104072-104082. [10.1016/j.bioorg.2020.104072]
Synthesis, biological evaluation and docking studies of a novel class of sulfur-bridged diazabicyclo[3.3.1]nonanes
Calò, Girolamo;Galeotti, Nicoletta;
2020
Abstract
A small library of 3-thia-7,9-diazabicyclo[3.3.1]nonanes was synthesized and their opioid receptors affinity and selectivity evaluated. Among these novel sulfur-bridged compounds, the (E) 9-[3’-(3- chlorophenyl)-but-2’-en-1’-yl]-7-propionyl-3-thia-7,9-diazabicyclo[3.3.1]nonane 2i emerged as the derivative with the highest μ receptor affinity (Ki = 85 nM) and selectivity (Ki μ/δ = 58.8, Ki μ/κ > 117.6). The antinociceptive activity of 2i was also evaluated in acute thermal pain. Docking studies disclosed the specific pattern of interactions of these derivatives.File | Dimensione | Formato | |
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