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Among a series of C-alkylated analogs of the weak μ opioid ligand spiro[benzofuran-3(2H),4 -1 -methylpiperidine-7-ol] (1), the 2-methyl, 2-ethyl, and cis 3 -methyl analogs, namely compounds (±)2, (±)-3, and (±)-4, showed much enhanced μ-affinities, with (±)-4 being almost as potent as (-)-morphine; while the trans 3 -methyl analog (±)-5 remained a weak μ-binder. Energy calculations and nmr data indicated that compounds 2-4 favor phenyl-axial conformations, while compounds 1 and 5 favor phenyl-equatorial conformations.
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