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Starting from (MeO) 3 SiCH 2 Cl (10) and Ph 2 (H)SiCH 2 OH (16), respectively, the (hydroxymethyl)diphenyl(piperidinoalkyl)silanes (HOCH 2 )Ph 2 Si(CH 2 ) 2 NC 5 H 10  (6) and (HOCH 2 )Ph 2 Si(CH 2 ) 3 NC 5 H 10  (8) have been synthesized [10→Ph 2 (MeO)SiCH 2 Cl (11)→Ph 2 (CH 2 =CH)SiCH 2 Cl (12)→Ph 2 (CH 2 =CH)SiCH 2 OAc (13)→Ph 2 (CH 2 =CH)SiCH 2 OH (14)→Ph 2 (CH 2 =CH)SiCH 2 OSiMe 3  (15)→6; 16→Ph 2 (H)SiCH 2 OSiMe 3  (17)→8; NC 5 H 10  = piperidino]. N-Quaternization of 6 and 8 with MeI gave the corresponding methiodides 7 and 9, respectively. As shown by IR-spectroscopic studies, compounds 6 and 8 form intramolecular O-H···N hydrogen bonds in solution (CCl 4 ). In the crystal, 6 (space group Pna2 1 ; two crystallographically independent molecules) also forms intramolecular O-H···N hydrogen bonds whereas 8 (space group P1̅) forms intermolecular O-H···N hydrogen bonds leading to the formation of centrosymmetric dimers (single-crystal X-ray diffraction studies). The (hydroxymethyl) silanes 6-9 and the related silanols (HO)Ph 2 Si(CH 2 ) 2 NC 5 H  10  (sila-pridinol; 1), sila-pridinol methiodide (2), (HO)Ph 2 Si(CH 2 ) 3 NC 5 H 10  (sila-difenidol; 3) and sila-difenidol methiodide (4) were investigated for their antimuscarinic properties. In functional pharmacological experiments as well as in radioligand competition studies, all compounds behaved as simple competitive antagonists at muscarinic M 1 -, M 2 -, M 3 - and M 4 -receptors. In general, the silanols 1-4 displayed higher receptor affinities (up to 100-fold) than the corresponding (hydroxymethyl) silanes 6-9 . In the (hydroxymethyl)silane series, compound 7 was found to be the most potent muscarinic antagonist [pA 2 /pK i = 8,71/8,6 (M 1 ), 8,23/7,8 (M 2 ), 8,19/7,8 (M 3 ); pK i  = 8,2 (M 4 )]. In the silanol series, the related compound 2 showed the most interesting antimuscarinic properties [pA 2 /pK i  = 10,37/9,6 (M 1 ), 8,97/8,8 (M 2 ), 9,08/8,8 (M 3 ); pK i  = 9,4 (M 4 )].

zeitschrift für naturforschung b

(Hydroxymethyl)diphenyl(piperidinoalkyl)silane des Typs (HOCH 2 )(C 6 H 5 ) 2 Si(CH 2 ) n NC 5 H 10 (n=2,3) und deren Methoiodide: Synthese, Struktur und antimuscarinische Eigenschaften / (Hydroxymethyl)diphenyl(piperidinoalkyl)silanes of the Type (HOCH 2 )(C 6 H 5 ) 2 Si(CH 2 ) n NC 5 H 10 (n = 2,3) and their Methiodides: Synthesis, Structure and Antimuscarinic Properties