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, G.; Asproni, B.; Corona, P.; Gessi, S.; Merighi, S.; Battistello, E.; Sturaro, C.; Calo, G.; Galeotti, N.; Temml, V.; Herdlinger, S.; Schuster, D.; Pinna, G. A.. - In: BIOORGANIC CHEMISTRY. - ISSN 0045-2068. - 102:(2020), p. 104072. [10.1016/j.bioorg.2020.104072]

Synthesis, biological evaluation and docking studies of a novel class of sulfur-bridged diazabicyclo[3.3.1]nonanes

Murineddu G.;Asproni B.;Corona P.;Pinna G. A.
2020-01-01

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.
2020
Synthesis, biological evaluation and docking studies of a novel class of sulfur-bridged diazabicyclo[3.3.1]nonanes / Murineddu, G.; Asproni, B.; Corona, P.; Gessi, S.; Merighi, S.; Battistello, E.; Sturaro, C.; Calo, G.; Galeotti, N.; Temml, V.; Herdlinger, S.; Schuster, D.; Pinna, G. A.. - In: BIOORGANIC CHEMISTRY. - ISSN 0045-2068. - 102:(2020), p. 104072. [10.1016/j.bioorg.2020.104072]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11388/235956
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