TY - JOUR A1 - Tacke, Reinhold A1 - Zimonyi-Hegedüs, E. A1 - Strecker, M. A1 - Heeg, E. A1 - Berndt, B. A1 - Langner, R. T1 - Sila-Analogon des Tiemoniumiodids T1 - Sila-Analogue of Tiemonium Iodide N2 - Sila-Tiemoniumiodid (16b), ein Sila-Analogon des Anticholinergicums Tiemoniumiodid (16a), und das Sila-Analogon 14b der entsprechenden Tiemonium-Base 14a wurden erstmalig synthetisiert.14b und 16b sowie die Vorstufen 10-13 und 15 wurden in ihren physikalischen und chemischen Eigenschaften charakterisiert und in ihrer Struktur durch Elementaranalysen sowie \(^1\)H-NMR- und Massenspektren sichergestellt. Die spasmolytischen Eigenschaften der Paare 14a/14b und 16a/16b wurden am isolierten Meerschweinchendarm vergleichend untersucht. N2 - Silatiemonium iodide (16b), a sila-analogue of the anticholinergic tiemonium iodide (16a), and the siJa-analogue 14b of the corresponding free base 14a were synthesized for the first time. Compounds 14b and 16b as weil as their precursors 10-13 and 15 were characterized by their physical and chemical properties. Their structures were confirmed by elementary analyses, (^1\)H NMRand massspectroscopy. The spasmolytic properties of the pairs 14a/14b and 16a/16b were compared on the isolated guinea pig ileum. KW - Anorganische Chemie Y1 - 1980 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-63669 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Wuttke, F. A1 - Henke, H. T1 - Zur Stereochemie der mikrobiellen Reduktion von rac-Acetyl( t-butyl)methylphenylsilan mit Trigonopsis variabilis (DSM 70714) und Corynebacterium dioxydans (ATCC 21766): Aufklärung der absoluten Konfiguration der Biotransformationsprodukte (SiR,CR)- und ( SiS ,CR)-t-Butyl( 1-hydroxyethyl)methylphenylsilan N2 - No abstract available KW - Anorganische Chemie Y1 - 1992 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-64176 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Wiesenberger, Frank A1 - Lopez-Mras, Angel A1 - Sperlich, Jörg A1 - Mattern, Günter T1 - Neuartige zwitterionische λ5-Spirosilicate: Synthese und Kristallstruktur von Bis[1,2-benzoldiolato(2-)][2-(dimethylammonio)phenyl]silicat sowie Synthese von Bis[2,3-naphthalindiolato(2-)][2-(dimethylammonio)phenyl]silicat-Hemiacetonitril-Solvat N2 - No abstract available. KW - Silicate KW - Bis[1,2-benzenediolato(2-)][2-(dimethylammonio)phenyl]silicate KW - Bis[2,3-naphthalenediolato(2-)][2-(dimethylammonio)phenyl]silicate KW - zwitterionic λ5-Spirosilicates Y1 - 1992 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-86916 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Wiesenberger, Frank T1 - (Acetoxymethyl)methylphenylgerman: Synthese, thermisches Verhalten und olfaktorische Eigenschaften T1 - (Acetoxymethyl)methylphenylgermane: Synthesis, Thermal Behaviour and Olfactoric Properties N2 - No abstract available. KW - Chemische Synthese KW - Temperaturabhängigkeit KW - Olfaktorische Analyse KW - (Acetoxymethyl)methylphenylgermane KW - (Acetoxymethyl)methylphenylsilane KW - hydratropyl acetate KW - thermal stability KW - perfumes Y1 - 1991 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-86927 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Wiesenberger, F. A1 - Becker, B. A1 - Rohr-Aehle, R. A1 - Schneider, P. B. A1 - Ulbrich, U. A1 - Sarge, S. M. A1 - Cammenga, H. K. A1 - Koslowski, T. A1 - Niessen, W. von T1 - Ester von (Hydroxymethyl)diorganylsilanen: Synthese und thermisch induzierte Umlagerung T1 - Esters of (Hydroxymethyl)diorganylsllanes: Synthesis and Thermally Induced Rearrangement N2 - Twenty silanes of the type R\(^1\)R\(^2\)Si(H)CH\(_2\)OR\(^3\) (A) were syn- and entropy of activation) of these reactions were studied by thesized {R\(^1\), R\(^2\) = Me, Ph, 1-naphthyl, PhCH\(_2\), Me\(_3\)SiCH\(_2\); OR\(^3\) means of düferential scanning calorimetry (DSC). In addition, = OC(O)Me, OC(O)Ph, OC(O)CF\(_3\) , OS(0)\(_2\)CF\(_3\), OP(O)Ph\(_2\), the kinetics of all reactions were investigated by 1H-NMR OC(O)Cl, and studied for their thermal behaviour. The silanes spectroscopy. The transition state of the rearrangement was A undergo a thermally induced rearrangement to give the investigated by an ab initio study based on the model comcorresponding silanes R\(^1\)R\(^2\)Si(OR\(^3\))Me (B). For compounds with pound H\(_3\)SiCH\(_2\)OC(O)H (-> MeH\(_2\)SiOC(O)H]. The theoretical OR3 = OC(O)Cl, an additional decarboxylation takes place to data and the experimentally obtained energetic and kinetic yield the chlorosilanes R1R2Si(Cl)Me. Except for the deriva- data are discussed in terms of mechanistic aspects of the retives with OR\(^3\) = OC(O)Cl, the energetic (reaction enthalpy) arrangement reaction A -> B. and kinetic data (reaction order, frequency factor, enthalpy ... KW - Anorganische Chemie Y1 - 1992 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-64188 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Wannagat, U. T1 - Sila-Analoga des Mephenhydramins T1 - Sila-Analogues of Mephenhydramine N2 - 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). KW - Anorganische Chemie Y1 - 1975 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-63525 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Wannagat, U. T1 - Sila-Analoga des Chlorphenoxamins und des Clofenetamins T1 - Sila-Analogues of Ohlorphenoxamine and Clofenetamine N2 - 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). KW - Anorganische Chemie Y1 - 1976 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-63531 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Wannagat, U. T1 - Sila-Analoga des Mebrophenhydramins T1 - Sila-Analogues of Mebrophenhydramine N2 - 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. KW - Anorganische Chemie Y1 - 1976 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-63542 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Wannagat, U. T1 - Sila-Analogon des Cicloniumbromids T1 - Sila-Analogue of Ciclonium Bromide N2 - 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). KW - Anorganische Chemie Y1 - 1976 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-63556 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Wannagat, U. T1 - Derivate des Sila-Mephenhydramins und Sila-Chlorphenoxamins T1 - Derivatives of Sila-Mephenhydramine and Sila-Ohlorphenoxamine N2 - 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. KW - Anorganische Chemie Y1 - 1976 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-63562 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Wannagat, U. T1 - Isoelektronische Derivate des Sila-Clofenetamins und des Sila-Mebrophenhydramins T1 - Isoelectronic Derivatives of Sila-Clofenetamine and Sila-Mebrophenhydramine N2 - 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). KW - Anorganische Chemie Y1 - 1976 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-63574 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Wannagat, U. T1 - N-Quaternäre Derivate basischer Sila-benzhydryläther T1 - N-Quaternary Derivatives of Basic Silabenzhydryl Ethers N2 - 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. N2 - Quaternary ammonium salts 1-10 of some biologically active silabenzhydryl ethers were synthesized for the frrst time by the reaction of the corresponding free bases A-E with CH\(_3\)I, CH\(_3\)Br or CH\(_3\)Cl in CH\(_3\)CN. The structures of 1-10 were confirmed by elementary analysis and 1 HNMR spectroscopy. The pharmacological effects of some compounds were compared with those of the corresponding free bases and of analogaus carbon cornpounds. KW - Anorganische Chemie Y1 - 1977 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-63583 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Wagner, S. A. A1 - Sperlich, J. T1 - Synthese von (-)-(Acetoxymethyl)(hydroxy-methyl)methyl(phenyl)german [(-)-MePhGe(CH\(_2\)OAc)(CH\(_2\)OH)] durch eine Esterase-katalysierte Umesterung: Die erste enzymatische Synthese eines optisch aktiven Germans N2 - No abstract available. KW - Anorganische Chemie KW - Germane KW - optically active KW - Biotransformation KW - stereoselective Transesterification KW - enzymatic KW - Porcine liver esterase Y1 - 1994 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-64310 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Wagner, S. A. A1 - Brakmann, S. A1 - Wuttke, F. A1 - Eilert, U. A1 - Fischer, L. A1 - Syldatk, C. T1 - Synthesis of acetyldimethyl(phenyl)silane and its enantioselective conversion into (R)-(1-hydroxyethyl)dimethyl(phenyl)silane by plant cell suspension culytures of Symphytum officinale L. and Ruta graveolens L. N2 - Starting from chlorodimethyl(phenyl)silane (3), acetyldimethyl(phenyl)silane (l) was prepared by a two-step synthesis in a total yield of 90% [PhMe\(_2\)SiCl (3)-> PhMe\(_2\)SiCCOMe)=CH\(_2\) (4)-> PhMe\(_2\)SiC(O)Me (1)]. The prochiral acetylsilane 1 was transfonned enantioselectively into (R)-(1-hydroxyethyl)dimethyl(phenyl)silane [(R)-2] using plant cell Suspension cultures of Symphytum officinale L. or Ruta graveolens L. Under preparative conditions (300-mg scale, not optimized), (R)-2 was isolated in 15% (Symphytum) and 9% yield (Ruta), respectively. The enantiomeric purities of the products were 81% ee (Syrnphytum) and 60% ee (Ruta), respectively. KW - Anorganische Chemie Y1 - 1993 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-64299 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Strohmann, C. A1 - Sarge, S. A1 - Cammenga, H. K. A1 - Schomburg, D. A1 - Mutschler, E. A1 - Lambrecht, G. T1 - Darstellung und Eigenschaften der Enantiomere des selektiven Antimuscarinikums 1-Cyclohexyl-1-phenyl-4-piperidino-1-butanol (Hexahydro-Difenidol) N2 - No abstract available KW - Anorganische Chemie KW - Difenidol KW - (R)- and (S)-hexahydro- / Antimuscarinic properties / Muscarinic receptor subtypes Y1 - 1989 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-63950 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Strecker, M. A1 - Sheldrick, W. S. A1 - Ernst, L. A1 - Heeg, E. A1 - Berndt, B. A1 - Knapstein, C.-M. A1 - Niedner, R. T1 - Sila-Pridinol und Pridinol: Darstellung und Eigenschaften sowie Strukturen im kristallinen und gelösten Zustand T1 - Sila-Pridinol and Pridinol: Preparation and Properties as weil as Structures ln the Solid Stateand in Solution N2 - Sila-Pridinol (2 b), ein Sila-Analogon des Anticholinergicums Pridinol (2a), wurde auf zwei verschiedenen Wegen dargestellt. Die Kristall- und Molekülstrukturen von 2 a und 2 b wurden röntgenstrukturanalytisch bestimmt. 2a bildet im festen Zustand intramolekulare Wasserstoffbrückenbindungen aus, während sich in kristallinem 2 b zentrosymmetrische, durch intermolekulare H-Brückenbindungen verknüpfte cyclische Dimere finden. IR- und \8^1\)H-NMR-spektroskopische sowie kryoskopische Untersuchungen ergaben Informationen über die Strukturen von 2a und 2 b in verschiedenen Lösungsmitteln. - Die pharmakologischen und toxikologischen Eigen" schaften von 2a und 2b wurden unter dem Gesichtspunkt bekannter Struktur-Wirkungs-Beziehungen vergleichend untersucht. 2 b erwies sich als ein etwa fünfmal so starkes Anticholincrgicum wie 2a. N2 - Sila"pridinol (2 b), a sila"analogue of the anticholinergic pridinol (2a). was prepared by two different routes. The crystal and molecular structures of 2 a and 2 b were determined by X-ray structural analyses. 2a forms intramolecular hydrogen bonds in the solid state, whereas centrosymrnetric cyclic dimers linked through intermolecular hydrogen bonds are observed for crystalline 2 b. IR- and \(^1\)H NMR spectroscopic as weil as cryoscopic studies yielded information ab out the structures of 2a and 2 bin different solvents. - The pharmacological and toxicological properties of2a and 2b were compared with one another on the basis ofknown structure-activity relationships. The anticholinergic properties of 2b were found tobe about five times as strong as those of 2a. KW - Anorganische Chemie Y1 - 1980 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-63654 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Strecker, M. A1 - Niedner, R. T1 - Cholinesterase-hemmende Organophosphorsäureester und ihre Sila-Analoga T1 - Organophosphates with Anticholinesterase Activity and their Sila-Analogues N2 - Die Organophosphorsäureester la-4a und ihre Sila-Analoga lb-4b des Typs R\(^1\)R\(^2\)P(O)( p-OC\(_6\)H\(_4\)ElMe\(_3\)) (EI = C, Si) wurden synthetisiert. Die Kohlenstoff-Verbindungen 1 a- 4a zeigen hinsichtlich ihrer Anticholinesterase-Aktivität die gleichen Struktur-Wirkungs-Beziehungen wie die Silicium-Verbindungen 1 b- 4 b. Letztere sind jeweils wirksamer als die entsprechenden C-Analoga. N2 - The organophosphates la-4a and their sila-analogues lb-4b of the type R\(^1\)R\(^2\)P(O)( p-OC\(_6\)H\(_4\)ElMe\(_3\) (El = C, Si) were synthesized. With regard to their anticholinesterase activity, the carbon compounds ta- 4a exhibit the same structure-activity relationships as the silicon compounds 1 b- 4b. The latter are more activ than the corresponding C-analogues. KW - Anorganische Chemie Y1 - 1981 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-63689 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Strecker, M. A1 - Lambrecht, G. A1 - Moser, U. A1 - Mutschler, E. T1 - (2-Aminoethyl)-cycloalkylphenylsilanole: Bioisosterer C/Si-Austausch bei Parasympatholytika vom Typ des Trihexyphenidyls, Cycrimins und Procyclidins T1 - (2-Aminoethyl)cycloalkylphenylsilanols: Bioisosteric C/Si Exchange in Parasympatholy1ics of lhe Trihexyphenidyl, Cycrimine, and Procyclidine Type N2 - Die Synthese der (2-Aminoethyl)cycloalkylphenylsilanole Sb (Sila-Trihexyphenidyl), 6b (SilaCycrimin), 7 b (Sila-Procyclidin) und Sb wird beschrieben. Sb- Sb wurden - ausgehend von Cl\(_2\)(C\(_6\)H\(_5\))SiCH = CH\(_2\) (9) - durch eine fünfstufige Reaktionsfolge mit einer Gesamtausbeute von 32- 40% erhalten. Am isolierten Ileum des Meerschweinchens wurden die C/Si-Paare Sa, b- 8a, b vergleichend auf ihre antimuskarinische Aktivität geprüft. Die durch die Sila-Substilution von Sa-8a erreichte Zunahme der Affinität zum Muskarinrezeptor ist deutlich weniger ausgeprägt als bei den strukturverwandten C/Si-Paaren I a, b- 4a, b. N2 - Thc synthesis of thc (2-aminoethyl)cycloalkylphenylsilanols Sb (sila-trihexyphenidyl), 6b (silacycrimine), 7b (sila-procyclidine), and Sb is described. Starting with Cl2(C6H5)SiCH = CH2 (9), Sb- 8 b were obtained by five reaction steps with a total yield of 32- 40%. The C/Si pairs Sa,b- 8a, b were tested for antimuscarinic activity on the isolated guinea-pig ileum. Thc increase of affinity for the muscarinic reccptor caused by sila-substitution of S a- 8a is less marked than in the case of the structurally related C/Si pairs la,b-4a,b. KW - Anorganische Chemie Y1 - 1983 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-63741 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Strecker, M. A1 - Lambrecht, G. A1 - Moser, U. A1 - Mutschler, E. T1 - Bioisosterer C/Si-Austausch bei Parasympatholytika vom Typ des Pridinols T1 - Bioisosterie C/Si Exchange in Parasympatholytia of tbe Pridinol Type N2 - Die Synthese der (2·Aminoethyl)diphenylsilanole 3b und 4b wird beschrieben. Die parasympatholytischen Eigenschaften der CISi-Paare la/lb-4a/4b wurden am isolierten Ileum des Meerschweinchens untersucht. In allen Fällen führt der C/Si-Austausch zu einer Zunahme der Affinität zum Muskarin-Rezeptor. N2 - The synthesis of the (2·aminoethyl)diphenylsilanols 3b and 4b is described. The Q'Si pairs lallb-4a/4b were tested for atropine-like activity on the isolated guinea-pig ileum. In all cases the C/Si exchange Ieads to an increased affinity for the muscarine-sensitive acetylcholine receptor. KW - Anorganische Chemie Y1 - 1984 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-63766 ER - TY - JOUR A1 - Tacke, Reinhold A1 - Sperlich, Jörg A1 - Strohmann, Carsten A1 - Frank, Brigitta A1 - Mattern, Günter T1 - Bis[3,4,5,6-tetrabrom-1,2-benzoldiolato(2-)]-(pyrrolidiniomethyl)silicat-Acetonitril-Solvat [(C6Br4O2)2SiCH2(H)NC4H8 · CH3CN]: Synthese sowie Kristall- und Molekülstruktur eines zwitterionischen [lambda]5-Spirosilicats N2 - Single crystal X-ray studies on bis[3,4,5,6-tetrabromo-1 ,2-benzenediolato(2- )](pyrrolidiniomethyl)silicate acetonitrile solvate [(C6Br40 2hSiCH2(H)NC4H8 · CH3CN; monoclinic, P2t/c, a = 808.5(4), b = 1533.0(8), c = 2212.6(1) pm, ß = 97.67(2)0 , Z = 4] revealed a zwitterionic structure with a pentacoordinate, formally negatively charged silicon atom and a positively charged ammonium moiety. The silicon atom is surrounded by four oxygen atoms and one carbon atom in a trigonalbipyramidal fashion, with the carbon atom in an equatorial position. The structure is displaced by 7.0% from the trigonal bipyramid towards the square pyramid. The zwitterion and the CH3CN molecule form intermolecular N-H · · · N hydrogen bonds. KW - Kristallstruktur KW - Spirosilicate KW - crystal structure KW - zwitterionic spirosilicate Y1 - 1992 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-86884 ER -