Cinnamoyl derivatives of 7alpha-aminomethyl-6,14-endo-ethanotetrahydrothebaine and 7alpha-aminomethyl-6,14-endo-ethanotetrahydrooripavine and related opioid ligands.
Article Details
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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
Drug Target Property Measurement pH Temperature (°C) Morphine Kappa-type opioid receptor Ki (nM) 46.9 N/A N/A Details Morphine Kappa-type opioid receptor EC 50 (nM) 484 N/A N/A Details Morphine Mu-type opioid receptor Ki (nM) 1.1 N/A N/A Details Morphine Mu-type opioid receptor EC 50 (nM) 15.6 N/A N/A Details Morphine Mu-type opioid receptor EC 50 (nM) 316 N/A N/A Details