Bioorganic and Medicinal Chemistry Letters p. 1813 - 1818 (1998)
Update date:2022-07-29
Topics:
Tsai, Ya-Ching
Liou, Jing-Ping
Liao, Richard
Cheng, Chen-Yu
Tao, Pao-Luh
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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