Naltrexol and its C6 a and � desoxy, iodo, mesyl, tosyl, trifyl, dimethylcarbamyl and diphenylcarbamyl derivatives were studied in their energy minimized C ring chair-like and boat-like conformations using B3LYP/6-31G** and SM 5.4/A to estimate aqueous solvation free energy.  The resulting energy values were compared to experimental mu, kappa and delta opioid receptor binding affinities.  The total energy difference between � conformers correlated well with MOR binding affinity while the aqueous solvation free energy correlated well with the KOR binding affinity.

Relationships between opioid receptor affinity and calculated properties of 6α- and 6β-naltrexol and derivatives

243rd National Meeting (2012)

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