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  • 1
    ISSN: 1520-4804
    Quelle: ACS Legacy Archives
    Thema: Chemie und Pharmazie
    Materialart: Digitale Medien
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  • 2
    Digitale Medien
    Digitale Medien
    s.l. : American Chemical Society
    Journal of medicinal chemistry 38 (1995), S. 4944-4949 
    ISSN: 1520-4804
    Quelle: ACS Legacy Archives
    Thema: Chemie und Pharmazie
    Materialart: Digitale Medien
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  • 3
    Digitale Medien
    Digitale Medien
    s.l. : American Chemical Society
    The @journal of organic chemistry 52 (1987), S. 3442-3444 
    ISSN: 1520-6904
    Quelle: ACS Legacy Archives
    Thema: Chemie und Pharmazie
    Materialart: Digitale Medien
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  • 4
    ISSN: 1573-904X
    Schlagwort(e): lipophilicity ; liposomes ; intermolecular forces ; ionic bonds ; hydrogen bonds ; hydrophobic interactions ; pH-metric method ; NMR relaxation rates
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Chemie und Pharmazie
    Notizen: Abstract Purpose. The objective of this study was to compare and interpret the variations in lipophilicity of homologous (p-methylbenzyl)alkylamines (MBAAs) in isotropic (octanol/water) and anisotropic (zwitterionic liposomes/water) system. Methods. Two experimental approaches were used, namely the pH-metric method to measure lipophilicity parameters in octanol/water and liposomes/water systems, and changes in NMR relaxation rates to validate the former method and to gain additional insights into the mechanisms of liposomes/water partitioning. Results. For long-chain homologues (N-butyl to N-heptyl), the octanol/ water and liposomes/water systems mostly expressed hydrophobicity. In contrast, the lipophilicity of the shorter homologues (N-methyl to N-propyl) in the two systems expressed various electrostatic and polar interactions. Conclusions. The study sheds light on the molecular interactions between zwitterionic liposomes and amphiphilic solutes in neutral and cationic form.
    Materialart: Digitale Medien
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  • 5
    ISSN: 1573-904X
    Schlagwort(e): nitric oxide ; NO ; benzofuroxans ; NO donors
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Chemie und Pharmazie
    Notizen: Abstract Purpose. To investigate the effect of benzofusion on NO donor properties and related biological activities of the furoxan system. The biological properties considered were the ability to increase the cytosolic levels of cGMP in C6 cells and vasodilation. Methods. NO donor properties were investigated either in the presence or the absence of cysteine by using the Griess reaction, chemiluminescence, and gas chromatography. Increase of cytosolic cGMP levels were evaluated by radioimmunoassay. Vasodilating activity was assessed on rat aorta strips precontracted with noradrenaline, in the presence and the absence of oxyhemoglobin (HbO2) and methylene blue (MB), respectively. Results. Benzofuroxan and its methyl and cyano derivatives were unable to release NO under the experimental conditions. Generally these compounds displayed feeble vasodilating properties and were able to weakly stimulate soluble guanylate cyclase (sGC). By contrast, benzodifuroxan and benzotrifuroxan were able to produce both NO• and its reduced form NO−, the nitroxyl anion. They displayed potent vasodilating properties and were able to increase cytosolic levels of cGMP in a concentration-dependent manner. Conclusions. The simple benzofuroxans considered here are devoid of the capability to release NO, they weakly stimulate sGC as well as manifest feeble vasodilating properties by a mechanism that does not involve a thiol-induced NO production. By contrast, benzodifuroxan and benzotrifuroxan behave as typical NO donor furoxans.
    Materialart: Digitale Medien
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  • 6
    Digitale Medien
    Digitale Medien
    Springer
    Structural chemistry 1 (1990), S. 417-421 
    ISSN: 1572-9001
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Chemie und Pharmazie
    Notizen: Abstract The dipole moments of para-substituted azoxybenzenes (1, a-e) and phenylazoxycyanides (2, a-e) were analyzed in terms of bond moments and additional contributions expressing electron delocalization. The results are compatible with a significant participation of the polar mesomeric formula B (25% or 34% for1 and2, respectively), the N-O bond acquiring considerable double-bond character. Comparison of known x-ray structures reveals that this bond is significantly shortened, whereas the N=N bond is extended only very slightly. Hence we can consider the possibility that the N1 atom allocates somewhat more than eight valence electrons, similarly to nitro compounds. In all respects the properties of the azoxy group are between those of the nitro and imino-N-oxide groups.
    Materialart: Digitale Medien
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  • 7
    ISSN: 1573-904X
    Schlagwort(e): NO-donors ; β-blockers ; hybrid drugs ; furoxans ; vasodilation
    Quelle: Springer Online Journal Archives 1860-2000
    Thema: Chemie und Pharmazie
    Notizen: Abstract Purpose. A series of derivatives having a propranolol-like moiety linked to NO-donor furoxan substructures were synthesized. The main objective of this investigation was to obtain agents with mixed NO-dependent vasodilating and β-blocking activities. Methods. Most of the target compounds were synthesized from the appropriate furoxans bearing XCH2CH2NH2 (X = O, S, SO2) chains at the 4 position of the ring, using A1(C2H5)3 in methylene chloride solution and (±)2,3-epoxypropyl 1-naphtyl ether. Two of the final products (X = CONH) were obtained by coupling the appropriate furoxancarboxylic acids with N-[2-hydroxy-3-(l-naphthoxy)propyl]-ethylenediamine. β1- and β2-blocking activities were examined on isolated guinea pig right atria and on guinea pig trachea respectively. Vasodilating properties were assessed on endothelium denuded strips of rat aorta. Results. Some derivatives behave as well balanced 'hybrids' displaying NO-dependent vasodilating and β-blocking properties in the same concentration range. Some others display either prevalent β-blocking or vasodilating activity. Generally speaking hybrid formation lowers the affinity for β-receptors, in particular for β2-type, to give an increase in β1/β2 selectivity. Conclusions. The furoxan system is a flexible tool in designing analogues of propranolol whose NO-donating and β-blocking properties are modulated over a wide range.
    Materialart: Digitale Medien
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  • 8
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 1211-1213 
    ISSN: 0170-2041
    Schlagwort(e): Furoxan, derivatives ; Furazan, derivatives ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The synthesis and structure of the two isomeric phenylfuroxancarbaldehydes 7a and 7b, of the phenylfurazancarbaldehyde 6 and of the corresponding alcohols 3a, 3b and 5 are reported. Thermal equilibration of the furoxan derivatives and their oxidation to the corresponding carboxylic acids 8a and 8b are also discussed.
    Materialart: Digitale Medien
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  • 9
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 1017-1023 
    ISSN: 0170-2041
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Beschreibung / Inhaltsverzeichnis: Eine Untersuchung zur Struktur von Tryllers und Schmitz' Verbindungen sowie von verwandten SubstanzenNMR-spektroskopische Untersuchungen zeigen, daß Tryllersche und Schmitzsche Verbindungen Furoxan- (3) beziehungsweise 1,4,2,5-Dioxadiazin-Struktur (11) besitzen. NMR- und röntgenkristallographische Untersuchungen zeigen, daß es sich bei den durch Einwirkung von Stickstoffetroxid und 5proz. Natronlauge auf die Tryllersche Verbindung erhaltenen Produkten um Furazano[3,4-d]pyridazin-1,5,6-trioxid (5) beziehungsweise Furazano[3,4-d]pyridazin-5,6-dioxid (8) handelt. Mit den gleichen Methoden wird auch gezeigt, daß dem durch Einwirkung von Stickstofftetroxid auf die Schmitzsche Verbindung erhaltenen Produkt die 1,4,2,5-Dioxadiazin-Struktur 12 zugeordnet werden kann.
    Notizen: NMR spectroscopic studies show that Tryller's and Schmitz's compounds have furoxan (3) and 1,4,2,5-dioxadiazine (11) structures, respectively. Combined NMR spectroscopy and X-ray crystallography show that the products obtained by action of dinitrogen tetroxide and 5% sodium hydroxide on Tryller's compound have furazano[3,4-d]pyridazine 1,5,6-trioxide and furazano[3,4-d]pyridazine 5,6-dioxide structures 5 and 8, respectively. They also show that the product obtained by action of dinitrogen tetroxide on Schmitz's compound has a dinitroethyl-1,4,2,5-dioxadiazine structure 12.
    Zusätzliches Material: 3 Ill.
    Materialart: Digitale Medien
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  • 10
    Digitale Medien
    Digitale Medien
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 24 (1986), S. 919-920 
    ISSN: 0749-1581
    Schlagwort(e): 17O NMR Chemical Shifts ; deuterium isotope effects ; Chemistry ; Analytical Chemistry and Spectroscopy
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Large deuterium isotope effects on 17O resonances were observed for six common NMR solvents. Only in the case of acetone did the substitution of deuterium for hydrogen result in a downfield shift. The H/D isotope effect was also detected in a study of the reversible hydration of CH3CHO.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
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