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Biological recognition of enantiomeric silanes and Germanes: Syntheses and antimuscarinic properties of the enantiomers of the si/ge analogues cyclohexyl(hydroxymethyl)phenyl(2-piperidinoethyl)silane and -germane and their methiodides

par Reichel, Dirk;Tacke, Reinhold;Jones, Peter P.G.;Lambrecht, Günter;Gross, Jan;Mutschler, Ernst;Waelbroeck, Magali
Référence Organosilicon Chemistry II, Wiley Blackwell, page (231-236)
Publication Publié, 2008-04

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Résumé :

The enantiomers of the Si/Ge analogues cyclohexyl(hydroxymethyl)phenyl-(2-piperidinoethyl)silane and -germane and their methiodides were synthesized and investigated with respect to their affinities at muscarinic M1, M2, and M3 receptors. The compounds displayed pronounced stereoselective antimuscarinic action, the (R)-enantiomers being more potent than the corresponding (S)-antipodes. The receptor affinities of the respective Si/Ge analogues were found to be very similar, indicating a strongly pronounced Si/Ge bioisosterism.