| Abstract
| - Sila-substitution (C/Si exchange) at the 4-position of the piperidine skeleton of the σ receptor ligandpanamesine (1a, EMD 57445) leads to sila-panamesine (1b). Compounds 1a and 1b were synthesized inmultistep syntheses, starting from 1-benzyl-4-piperidone and tetramethoxysilane, respectively, and wereisolated as the hydrochlorides 1a·HCl and 1b·HCl. ESI-MS studies of aqueous solutions of the silanol1b and the corresponding disiloxane 14 at different pH values revealed a remarkable stability of 1b. Theidentities of 1a·HCl and 1b·HCl were established by elemental analyses and multinuclear NMR studies.The σ1 and σ2 receptor affinities of the C/Si analogues panamesine (1a) and sila-panamesine (1b) weredetermined in competitive radioligand receptor binding studies. It was shown that the C/Si exchangeresults in a 3-fold enhancement of σ1 receptor affinity.
- The σ receptor ligand panamesine (1a, EMD 57445) and its silicon analogue sila-panamesine (1b) were synthesized in multistep syntheses and isolated as the hydrochlorides 1a·HCl and 1b·HCl. The identities of 1a·HCl and 1b·HCl and their precursors were established by elemental analyses and multinuclear NMR studies, and the σ1 and σ2 receptor affinities of the C/Si analogues panamesine and sila-panamesine were determined in competitive radioligand receptor binding studies.
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