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- W2950240219 abstract "Two series of σ(1) ligands with a spiro[[2]benzopyran-1,3'-pyrrolidine] (3) and a spiro[[2]benzofuran-1,3'-pyrrolidine] (4) framework were synthesized and pharmacologically evaluated. Several reaction steps were considerably improved by microwave irradiation. The σ(1) affinity of the spirocyclic ligands correlates nicely with the benzene-N-distance, i.e. 2 < 3 < 4 < 1. The σ(1) affinity of both compound classes could be increased with large N-substituents (e.g. 2-phenylethyl, octyl). Nevertheless the benzyl derivative 4a represents the most promising σ(1) ligand (K(i) = 25 nM) due to its high selectivity against the σ(2) subtype (>40-fold), the NMDA receptor and 5-HT(6) and 5-HT(7) receptors. Moreover, 4a did not inhibit the hERG channel in the heart." @default.
- W2950240219 created "2019-06-27" @default.
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- W2950240219 date "2012-07-01" @default.
- W2950240219 modified "2023-10-16" @default.
- W2950240219 title "Microwave assisted synthesis of spirocyclic pyrrolidines – σ1 receptor ligands with modified benzene-N-distance" @default.
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- W2950240219 doi "https://doi.org/10.1016/j.ejmech.2012.04.018" @default.
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