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Die Umsetzung von Diphenyl-vinylsilan mit zyklischen sekundären Aminen (z.B. Morpholin) in Gegenwart der entsprechenden Lithium-amide führt zu einer Substitution des an Silicium gebundenen H-Atoms durch eine Aminogruppe und zu einer Addition des Amins an die Vinylgruppe. 2-Thienylphenyl- vinylsilan reagiert jedoch zusätzlich unter Spaltung der Si-e-Bindung und Aminosubstitution der 2-Thienylgruppe.
Die quartären Ammoniumsalze 1-10 einiger bioaktiver Sila-benzhydryläther wurden erstmalig durch Reaktion der entsprechenden freien Basen A-E mit CH\(_3\)J, CH\(_3\)Br bzw. CH\(_3\)Cl in CH\(_3\)CN dargestellt. Die Strukturen von 1-10 wurden durch Elementaranalysen und 1 H-NMR-Spektren bestätigt. Die pharmakologischen Effekte einiger Verbindungen wurden sowohl mit den Eigenschaft der entsprechenden freien Basen als auch mit einigen Struktur-Wirkungsbeziehungen analoger Kohlenstoffverbindungen verglichen.
Isoelectronic derivatives (A and B) and a homolog (C) of the two sila-antihistamines sila-clofenetamine and silamebrophenhydramine were synthesized for the first time by the steps shown in scheme 1. They and their unknown precursors II-IV were characterized by their physical (Table 1) and chemical properties and their structures confinned by lH-NMR and rnass spectroscopy (Tables 2 and 3). The pharrnacological effects of A and B were investigated and compared with those of the corresponding 0-isosteric sila-antihistarnines (Chapter 5).
Derivatives A and B of the two sila-antihistam.ines silamephenhydramine and sila-chlorphenoxamine were synthesized for the first time by the steps shown in scheme 1. They and their precursors III and IV were characterized by their physical (Table 1) and chemical properties and their structures confirmed by NMR and mass spectroscopy (Tables 2 and 3). Their pharmacological effects were investigated and compared with those of the corresponding sila-antihistamines.
Sila-Analogues B 2 and A 2 of the spasmolytic ciclonium bromide (B 1) respectively the corresponding free base A 1 were synthesized for the first time according to the reaction steps sho·wn in scheme 1, and they and their precursors I and II were characterized by ph;ysical (Table 1} and chemical properties and their structures confirmed by NMR, and mass spectroscopy (Tables 2 and 3}. The pharmacological effects of A 2 and B 2 were investigated and compared with those of the parent carbon compound B 1 (chapter 5).
Sila-analogues A 2, B 2 and C 2 of the drug mebrophenhydramine from the class of benzhydryl ethers -were synthesized for the first time by the steps shown in scheme 1, and they and their precurso:rs I-Ill were characterized by their physical (Table 1) and chemical properties, a.nd their structures confirmed by NMR, mass and infrared spectroscopy (Tables 3-5). The histaminolytic and anticholinergic effects of A 2 and C 2 were investigated and compared with some structure-activity relationships of analogue carbon compounds.
Sila-ana.logues A 2 and B 2 of two drugs from the benzhydryl ether class, chlorphenoxamine and clofenetamine, were synthesized for the first time by the steps shown in scheme 1. They and their precursors I-VI v;rere characterized by their physical (Table 1) and chemical properties and their structures confirmed by n.m.r., mass and infrared spectroscopy (Tab]es 2-5). Their physiological effects were invest.igated and compared with those of the carbon analogues (Chapter 5).
Sila-Analogues A 2, B 2 and C 2 of the drug mephenhydramine from the class of benzhydryl ethers were synthesized for the first time by the steps shown in scheme 1, and they and their precursors I-V characterized by their physical {table 1) and chemical properties, and their structures confirmed by NMR, n1ass and infrared spectroscopy (tables 3-5). Their physiological effects were investigated a.nd compared -with those of the parent carbon compounds (section 5).
It is shown by means of IR. spectroscopic methodsthat nigericin and monensin bave a cyclic conformation similar to that of their silver salts. Camplex fonnation constants with sodium and potassium ions follow the selectivity order determined by EMF. measurements on liquid membranes: nigericin: K\(^+\) >Rb\(^+\)> Na\(^+\)> Cs\(^+\) >Li\(^+\); monensin: Na\(^+\)> K\(^+\) >Li\(^+\)> Rb\(^+\)> Cs\(^+\). Transport experiments show that nigericin and monensin facilitate the diffusion of potassium ions across model membranes, although in electrolytic transport experiments the permeability is not affected.
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