R. Tacke, Vera I. Handmann, R. Bertermann
Jan 28, 2003
Citations
0
Influential Citations
43
Citations
Journal
Organometallics
Abstract
The 1‘-organylspiro[indane-1,4‘-piperidine] derivatives 1a−4a (organyl = benzyl (1a), 4-methoxybenzyl (2a), 2-phenylethyl (3a), 3-methylbut-2-enyl (4a)) are high-affinity, selective σ ligands. The corresponding sila-analogues 1b−4b (→ replacement of the carbon spirocenter by a silicon atom) were synthesized in three-step syntheses, starting from dichlorodivinylsilane, and were isolated as the hydrochlorides 1b·HCl−4b·HCl. To get information about the structure of the title compounds and their respective carbon analogues in the solid state and in solution, crystal structure analyses (1a·HCl, 2a, 2b·HCl) and temperature-dependent solution 1H NMR studies (2a·HCl, 2b·HCl) were performed. These structural investigations were complemented by computational studies of related model species. The C/Si pairs 1a/1b−4a/4b were studied for their affinities for various central nervous system receptors (σ, 5-HT1A, 5-HT2A, α1, α2, M, D2) using radioligand binding assays. The σ affinities of the sila-analogues 2b−4b were f...