Preparation and diastereoselective birch reduction - Alkylation of chiral 3,4-dihydro-1(2H)-isoquinolinones. Enantiospecific syntheses and opioid receptor affinities of several hydro-2,3-dimethyl-1H-7,12α- methanobenzo[6,7]cycloocta[1,2-c]pyridine-9-ols
For a similar pseudoaxial conformation of the C(3) benzyl substituent of a N(4) methyl diketopiperazine observed in both the solid state and solution phase, see: Budesinsky, M.; Symersky, J.; Jecny, J.; VanHecke, J.; Hosten, N.; Angeunis, M.; Borremans, F. Int. J. Peptide Protein Res. 1992, 39, 123.
(S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid (13a) is available in high enantiomeric purity from the Nutra Sweet Company and Aldrich Chemical Co.
(S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid (13a) is available in high enantiomeric purity from the Nutra Sweet Company and Aldrich Chemical Co.
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Tangari, N.; Tortorella, V. J. Chem. Soc., Chem. Commun. 1975, 71-72.
(c) Benson, W. M.; Stefko, P. L.; Randall, L. O. J. Pharmacol. Exp. Ther. 1953, 109, 18914) The meperidines and methadons contain an arylpropylamine unit.
3H-labeled ligand; see: (a) Terenius, L. Acta Pharmacol. Toxicol. 1973, 32, 317. (b) Pert, C. B.; Snyder, S. H. Science 1973, 179, 1011-1014. (c) Simon, E. J.; Hiller, J. M.; Edelman, I. Proc. Natl. Acad. Sci., U.S.A. 1973, 70, 1947-1949.
3H-labeled ligand; see: (a) Terenius, L. Acta Pharmacol. Toxicol. 1973, 32, 317. (b) Pert, C. B.; Snyder, S. H. Science 1973, 179, 1011-1014. (c) Simon, E. J.; Hiller, J. M.; Edelman, I. Proc. Natl. Acad. Sci., U.S.A. 1973, 70, 1947-1949.
3H-labeled ligand; see: (a) Terenius, L. Acta Pharmacol. Toxicol. 1973, 32, 317. (b) Pert, C. B.; Snyder, S. H. Science 1973, 179, 1011-1014. (c) Simon, E. J.; Hiller, J. M.; Edelman, I. Proc. Natl. Acad. Sci., U.S.A. 1973, 70, 1947-1949.
(a) For a discussion of μ-opioid receptor models, see: Aldrich, J. V. In Burger's Medicinal Chemistry and Drug Discovery; Wolff, M. E., Ed.; Wiley: New York, 1996; Vol. 3, pp 369-372. For a discussion of uncertainty associated with the importance of nitrogen lone pair orientation with respect to analgesic activity, see: