Cinnamoyl derivatives of 7alpha-aminomethyl-6,14-endo-ethanotetrahydrothebaine and 7alpha-aminomethyl-6,14-endo-ethanotetrahydrooripavine and related opioid ligands.

Article Details

Citation
Copy to clipboard

Rennison D, Neal AP, Cami-Kobeci G, Aceto MD, Martinez-Bermejo F, Lewis JW, Husbands SM

Cinnamoyl derivatives of 7alpha-aminomethyl-6,14-endo-ethanotetrahydrothebaine and 7alpha-aminomethyl-6,14-endo-ethanotetrahydrooripavine and related opioid ligands.

J Med Chem. 2007 Oct 18;50(21):5176-82. Epub 2007 Sep 22.

PubMed ID
17887741 [ View in PubMed
]
Abstract

A new series of ligands has been synthesized where the cinnamoyl group of the 14-cinnamoylamino morphinones has been introduced to the 7alpha-substituent of the 6,14-bridged oripavine series. In vitro the compounds were mostly low efficacy partial agonists or antagonists with some selectivity for the mu opioid receptor, with evidence of micro efficacy in vivo. The similarity in SAR between these 6,14-bridged oripavines and the 14-cinnamoylamino series suggests a similar mode of interaction with the micro opioid receptor.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
MorphineKappa-type opioid receptorKi (nM)46.9N/AN/ADetails
MorphineKappa-type opioid receptorEC 50 (nM)484N/AN/ADetails
MorphineMu-type opioid receptorKi (nM)1.1N/AN/ADetails
MorphineMu-type opioid receptorEC 50 (nM)15.6N/AN/ADetails
MorphineMu-type opioid receptorEC 50 (nM)316N/AN/ADetails