C-alkylated spiro[benzofuran-3(2H),4'-1'-methyl-piperidine-7-ols] as potent opioids: a conformation-activity study.
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Tsai YC, Liou JP, Liao R, Cheng CY, Tao PL
C-alkylated spiro[benzofuran-3(2H),4'-1'-methyl-piperidine-7-ols] as potent opioids: a conformation-activity study.
Bioorg Med Chem Lett. 1998 Jul 21;8(14):1813-8.
- PubMed ID
- 9873439 [ View in PubMed]
- Abstract
Among a series of C-alkylated analogs of the weak mu 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 mu-affinities, with (+/-)-4 being almost as potent as (-)-morphine; while the trans 3'-methyl analog (+/-)-5 remained a weak mu-binder. Energy calculations and nmr data indicated that compounds 2-4 favor phenyl-axial conformations, while compounds 1 and 5 favor phenyl-equatorial conformations.
DrugBank Data that Cites this Article
- Binding Properties
Drug Target Property Measurement pH Temperature (°C) Meperidine Kappa-type opioid receptor Ki (nM) >100000 N/A N/A Details Meperidine Mu-type opioid receptor Ki (nM) 451 N/A N/A Details Morphine Kappa-type opioid receptor Ki (nM) 1870 N/A N/A Details Morphine Mu-type opioid receptor Ki (nM) 38 N/A N/A Details