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  • 1
    Electronic Resource
    Electronic Resource
    Cytostatic activity against HeLa cells of a series of indazole and indole derivatives; synthesis and evaluation of some analogues (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 817-824 
    Details
    ISSN: 0947-3440
    Keywords: Indazolols ; Indazolinones ; Indoxyls ; Cytostatic agents ; HeLa cells ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The remarkable cytostatic activity of 1-substituted indazolols 2a,b, condensed indazolinones 4a-c and indoxyl derivatives 5a, b against HeLa cells is reported. Three different approaches to the synthesis of indazolophthalazinone 4a, representing alternatives to those previously reported, were studied. Several compounds related to the mentioned indazolols and indazolinones were obtained and their cytostatic activity against HeLa cells was tested. Among them we can mention the tetracyclic SO2 analogue 14 and the condensed pyridine derivative 18, the tricyclic pyrazolophthalazinone 22 and the bicyclic pyrazolodiazepinone 25, which were prepared by taking advantage of the reactivity of heterocyclic spiro aminimides.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199505119
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  • 2
    Electronic Resource
    Electronic Resource
    A new class of network-polymeric chiral stationary phases (1995)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 7 (1995), S. 248-256 
    Details
    ISSN: 0899-0042
    Keywords: chiral discrimination ; chiral stationary phase ; network polymer ; DATD ; hydrogen bonding ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A strategy based on the use of homo bi- and multifunctional building blocks for the synthesis of a new class of network-polymeric chiral stationary phases has been evaluated. The key steps comprise acylation of N,N′-diallyl-L-tartardiamide (DATD) and reaction with a multifunctional hydrosilane, yielding a network polymer incorporating the bifunctional C2-symmetric chiral selector. Covalent bonding to a functionalized silica takes place during the latter process. Many of these chiral sorbents show interesting enantioselective properties toward a wide variety of racemic solutes under normal-phase (hexane-based) conditions. The retention is mainly caused by the hydrogen-bonding ability of the analyte, which is regulated by mobile phase additives like alcohol or ether cosolvents. The most interesting chiral stationary phases, in terms of broad enantioselectivity, were obtained from O,O′-diaryol-DATD-derivatives, particularly those containing the 3,5-dimethylbenzoyl and the 4-(tert-butyl)benzoyl moieties. Since high column efficiencies can be obtained with these chiral sorbents, an α-value of ca. 1.2 is usually sufficient to produce baseline separation. A large number of neutral as well as acidic or basic drug racemates are resolved without derivatization. © 1995 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530070411
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  • 3
    Electronic Resource
    Electronic Resource
    Organonickel(II) Complexes with Anionic N-Donor Ligands. Hydration of coordinated nitriles at a nickel(II) site (1997)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 80 (1997), S. 2477-2485 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The hydroxo complex (Bu4N)2[Ni2(C6F5)4(μ-OH)2]reacts with 2,3,4,5,6-pentafluoro benzenamine (C6F5-NH2), 1,3-diaryltriaz-1-enes (ArNH—N=N—Ar, Ar = Ph, 4-MeC6H4, 4-MeOC6H4), 7-aza-1H-indole (= 1H-pyrrolo[2.3-b]pyridine; Hazind), N-phenylpyridin-2-amine(pyNHPh), and N-phenylpyridine-2-carboxamide (py-CONHPh) at room temperature in acetone to give the binuclear complexes (Bu4N)2[Ni2(C6F5)4(μ-C6F5NH)2] (1) and (Bu4N)2[{Ni(C6F5)2} 2(μ-OH)(μ-azind)] (2) and the mononuclear complexes Bu4N[Ni(C6F5)2(ArN3Ar)] (3-5), Bu4N[Ni(C6F5)2(pyNPh)] (6), and Bu4N[Ni(C6F5)2(pyCONPh)] (7). The hydroxo.complex (Bu4N)2[{Ni(C6F5)2-(μ-OH)}2] promotes the nucleophilic addition of water to pyridine-2-carbonitrile, 2-aminoacetonitrile, and 2-(dimethylamino)acetonitrile, and complexes 8-10 containing pyridine-2-carboxamidato, 2-aminoacetamidato and 2-(dimethylamino)acetamidato ligands are formed. Analytical (C, H, N) and spectroscopic (IR, 1H and 19F-NMR, and FAB-MS) data were used for structural assignments. A single-crystal X-ray diffraction study of (Bu4N)2[{Ni(C6F5)2}2(μ-OH)(μ-azind)] (2) established the binuclear nature of the anion; the two Ni-atoms are bridged by an OH group and a 7-aza-7H-indol-7-yl group, but the central Ni—O—Ni—N—C—N ring is not planar, the dihedral angle between the Ni—O—Ni and Ni—N—C—N—Ni planes being 84.4°.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19970800815
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  • 4
    Electronic Resource
    Electronic Resource
    Potential H1-Antihistaminic Drugs: Synthesis of 4-[(2,3-Dihydro-2-oxo-1H-benzimidazol-1-yl)alkoxycarbonyl]-1-(diphenylmethyl)piperazines by Selective Monoalkoxycarbonylation of α,ω-Dichloroalkanes by Phase-Transfer Catalysis (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 539-544 
    Details
    ISSN: 0170-2041
    Keywords: H1-Antihistaminic ; Piperazines ; Phase-transfer catalysis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Potentielle H1-Antihistaminica: Synthese von 4-[(2,3-Dihydro-2-oxo-1H-benzimidazol-1-yl)alkoxycarbonyl]-1-(diphenylmethyl)piperazinen durch selektive Phasen-Transfer-katalysierte Monoalkoxycarbonylierung von α,ω-DichloralkanenDie Synthese einer Reihe von neuen 4-[(2,3-Dihydro-2-oxo-1H-benzimidazol-1-yl)alkoxycarbonyl]-1-(diphenylmethyl)piperazinen 2 durch Phasen-Transfer-katalysierte Monoalkoxycarbonylierung von α,ω-Dichloralkanen wird beschrieben. Die Piperazine 2 ähneln Oxatomid1) (1) und sind potentielle H1-Antihistaminica. Ferner wurde eine Untersuchung zur regioselektiven Synthese von substituierten 1,3-Dihydro-1-isopropenyl-2H-benzimidazol-2-onen (5) durchgeführt.
    Notes: The synthesis of a series of new 4-[(2,3-Dihydro-2-oxo-1H-benzimidazol-1-yl)alkoxycarbonyl]-1-(diphenylmethyl)piperazines 2 by phase-transfer catalysed monoalkoxycarbonylation of α,ω-dichloroalkanes is described. Compounds 2 are related to oxatomide1) (1) and are potential histamine-H1 antagonists. A study on the regioselective preparation of substituted 1,3-dihydro-1-isopropenyl-2H-benzimidazol-2-ones (5) was also carried out.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890195
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  • 5
    Electronic Resource
    Electronic Resource
    Nature et stabilité des complexes métalliques de cryptands dinucléants en solution. III. Le monocycle [22]-Py2N4 (1985)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 68 (1985), S. 840-845 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Nature and Stability of Some Metallic Complexes of Dinucleating Cryptands in Solution III. The Monocycle [22]-Py2N4The nature and stability of complexes formed by a new 22-membered monocycle L = [22]-Py2N4 with the cations Mn+ = Cu2+, Co2+, Ni2+, Zn2+, Cd2+, Pb2+, and Ag+ have been determined in aqueous solutions (0.01M NaClO4, 25°) by pH-metry and also, for the copper system, by UV-absorption spectrophotometry. The stepwise protonation constants of the four amine functions of L were 9.1, 8.3, 7.1 and 3.7 logarithms units, respectively. No evidence was found for the protonation of the two pyridine nitrogen atoms. Mononuclear complexes MLn+ were identified in all systems investigated, but the dinuclear species M2L2n+ were only found with Cu2+ and Ag+. The logarithms of the overall stability constants for the copper and silver complexes are CuL2+, 12.9; Cu2L4+, 18.6; Agl+, 6.3; Ag2L2+, 10.9, respectively. Mononuclear hydroxy species MLOH(n-1)+ were identified in all systems except those of copper and silver. No dinuclear hydroxy complexes were detected. The complexing properties of L are compared to those of the large and less rigid bis-dien.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19850680404
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  • 6
    Electronic Resource
    Electronic Resource
    Nature et stabilité des complexes métalliques de cryptands dinucléants en solution. I. Polyazapolyoxa macrotricycle cylindrique et monocycle constitutif (1985)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 68 (1985), S. 456-464 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Nature and Stability of Some Metallic Complexes of Dinucleating Cryptands in Solution. I. A Polyazapolyoxa Cylindrical Macrotricycle and its Monocyclic SubunitpH-metry and UV spectrophotometry were used to study the complexing properties of the cylindrical macrotricycle, 1,7,13,19-tetraaza-4,16-dioxa-10,22,27,32-tetraoxatricyclo[17.5.5.5]tetratriacontane (1) and of its constitutive monocyclic subunit, 1,7-diaza-4,10-dioxacyclododecane (2) with some transition and heavy metal cations (Cu2+, Co2+, Ni2+, Zn2+, Cd2+, Pb2+, Ag+), in aqueous medium 0.1M Et4NClO4, at 25°. The protonation constants of the ligands as well as the nature and the stabilities of the complexes formed in the pH-regions studied were determined. The tricycle 1 only formed dinuclear M2L complexes with Cu2+, Zn2+, and Ag+, accompanied in the latter case by a protonated mononuclear MLH species, and with Cu2+ and Zn2+ at high pH-values by dinuclear hydroxo complexes. Only mononuclear complexes were evidenced with the other cations, ML being accompanied either by protonated or hydroxy mononuclear species. The mononuclear complexes of 1, when they existed, were more stable than the corresponding complexes of 2, except for cobalt which formed complexes of comparable stability with both ligands. In the other cases (Cd2+, Pb2+, Ag+), the stability differences between the complexes of 1 and 2 increased with the size of the cation.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19850680219
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  • 7
    Electronic Resource
    Electronic Resource
    Heteroaromatic Nucleophilic Substitution Reactions by Phase-Transfer Catalysis- Synthesis of New Alkoxypridazin-3(2H)-ones (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 1465-1473 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heteroaromatische nucleophile Substitutionsreaktionen durch Phasen-Transfer-Katalyse- Synthese von neuen Alkoxypyridazin-3(2H)-onenDie Synthese von einigen 4- und 5-alkoxysubstituierten Pyridazin-3(2H)-onen mit hypotensiver und β-blockierender Wirkung durch Phasen-Transfer-Katalyse aus Halogenpyridazin-3(2H)-onen wird beschrieben. Der nucleophile Austausch verläuft recht glatt in der 5-Stellung aber viel langsamer in der 4-Stellung. Im Falle von 4,5-Dihalogenpyridazin-3(2H)-onen ergibt die Phasen-Transfer-Katalyse eine hohe Regioselektivität für die Substitution in 5-Stellung.
    Notes: The synthesis of several 4- and 5-alkoxy-substituted pyridazin-3(2H)-ones with hypotensive and β-blocking activities by phase-transfer catalysis (PTC) starting from halopyridazin-3(2H)-ones is described. The nucleophilic displacement reaction proceeds easily at the 5-position and remarkably slower at the 4-position. In the case of 4,5-dihalopyridazin-3(2H)-ones the PTC methods provide a high regioselectivity towards substitution in 5-position.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850717
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