Add time:09/24/2019 Source:sciencedirect.com
SummaryDiastereomeric forms of l-(pyrrolidin-1-ylmethyl)-2-(N-methyl)-4-[(3,4-dichloro)phenyl]-1,2,3,4-tetrahydroisoquinol in-3(2H)-ones 3a and its chloro analog 3c were synthesized. Compounds 3a,c are related to the κ-selective opiate ICI 199441 1 by linking the benzylic CH2 to the ortho position of the phenyl in 1. Compared with morphine, these compounds had lost in κ and κ affinities; only cis-3a showed a modest κ affinity. 1-Pyrrolidin-1-ylmethyl-N-[2-(3,4-dichlorophenyl)acetyl]-1,2,3, 4-tetrahydroisoquinoline 2, which is also a cyclic congener of 1, was reported to display high κ and μ affinity, and so a conformational study was undertaken on 1, 2 and 3a. This showed that, while active 2 extensively superposed on 1, 3a assumes another geometry which does not allow a fit with the pharmacophoric moieties of 1 and 2.
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