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  • 1
    ISSN: 1573-4919
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology , Medicine
    Notes: Summary The interaction between 4′-6-Diamidino-2-Phenylindole-hydrochloride (DAPI) and a variety of DNAs and synthetic polydeoxynucleotides was investigated in order to delineate the nucleic acid structural features necessary for binding. The spectra of DAPI-DNA complexes, measured at various DAPI-DNA molar ratios (r), are hypochromic relative to DNA in the region of its maximum absorption. All the curves pass through an isosbestic point at 268 nm. A new maxima appears in the region of 380–392 nm for DAPI-DNA complexes. The magnitude of the peaks in the region are directly proportional to the amount of drug present in the complex. Studies with various DNA types and synthetic polydeoxynucleotides indicate that the drug preferentially binds to dAT-rich regions of DNA. This was also confirmed by enzymatic studies. The inhibition of template action by DAPI in a purified DNA-polymerase reaction was dependent on the dAT-content of the template. The implication of these data to explain a selective binding of DAPI to mitochondrial DNA have been discussed.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Springer
    Fresenius' Zeitschrift für analytische Chemie 136 (1952), S. 194-199 
    ISSN: 1618-2650
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Springer
    Investigational new drugs 1 (1983), S. 103-115 
    ISSN: 1573-0646
    Keywords: diarylamidines ; diarylimidazolines ; murine leukemia L1210 ; DNA synthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology , Medicine
    Notes: Summary A series of 96 diarylamidine (and diarylimidazoline) derivatives were evaluated for their inhibitory effects on the growth and DNA synthesis of murine leukemia L1210 cells. The amidino- and imidazolino-substituted aryl moieties of the compounds consisted of phenyl, indole, indene, benzofuran, benzo[b]thiophene or benzimidazole. Several of these compounds were found to inhibit L1210 cell proliferation with an ID50 (50% inhibitory dose) of 1 μg/ml or lower. Structure-function analysis revealed that the antitumor cell activity of the diarylamidines depended on the planarity of the molecule, the presence of amidino- (or, preferably, imidazolino-) groups on both aryl moieties, the nature of the bridge connecting the two aryl moieties (preferably no bridge at all, phenoxy or ethene) and, finally, the nature of the aryl moieties (preferably, benzofuran or benzo[b]thiophene). Hence, compound 20 (6-(2-imidazolin-2-yl)-2-[4-(2-imidazolin-2-yl)phenyl] benzo[b]thiophene) emerged as the most potent inhibitor of L1210 cell growth (ID50: 0.21 μg/ml). Its inhibitory potency was similar to that of the well-known trypanocidal drug ethidium bromide (compound 98). For all diarylamidine derivatives taken together, some correlation (r = 0.612) was noted between the log ID50 for L1210 cell proliferation and the log ID50 for L1210 cell DNA synthesis (as monitored by [methyl 3H]dThd incorporation). These findings suggest that the inhibitory effects of the diarylamidines on L1210 cell proliferation may at least partially reside in an inhibition of DNA synthesis. Compound 41 (2,2′-vinylenedi-1-benzofuran-5-carboxamidine), that exhibited a potent antitumor activity in vitro (ID50: 1.5 μg/ml), was further evaluated for its antitumor efficacy in vivo and found to increase the median survival time of L1210 cell-inoculated BDF1 mice up to 204%, if administered at a dose of 200 mg/kg.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 3313-3328 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Chromanes, XVIII Synthesis of 7α-Methyl-6-oxaestroneReaction of 7-methoxy-2-methyl-4-oxochromane with vinylmagnesium bromide and then with 2-methyl-1.3-dioxocyclopentane resulted in the formation of 3-methoxy-7-methyl-17-oxo-6-oxaestra-1.3.5(10).8.14-pentaene (4b). Its catalytic hydrogenation led solely to the C//D-cis compounds 5 and 6. Only after hydrogenation of the 17-oxo group in 4b with sodium boron hydride to 8b did the catalytic hydrogenation yield the C//D-trans series 9b→10b→11b→7α-methyl-6-oxaestrone methyl ether (12b). An analogous sequence beginning with the tetrahydropyranyl ether 4c led via 8c→9c→10c→11a to 7α-methyl-6-oxaestrone (12a).
    Notes: Umsetzung von 7-Methoxy-2-methyl-chromanon-(4) mit Vinylmagnesiumbromid und dann mit 2-Methyl-cyclopentandion-(1.3) gab 3-Methoxy-7-methyl-6-oxa-östrapentaen-(1.3.5(10).8.14)-on-(17) (4b). Dessen katalytische Hydrierung ergab nur die C//D-cis-verknüpften Verbindungen 5 und 6. Erst nach Natriumborhydrid-Reduktion der 17-Ketogruppe in 4b zu 8b führte die katalytische Hydrierung in die C/D-trans-verknüpfte Reihe 9b→10b→11b→7α-Methyl-6-oxa-östron-methyläther (12b). Eine analoge Reaktionsfolge mit dem Tetrahydropyranyläther 4c lieferte auf dem Wege 8c→9c→10c→11a 7α-Methyl-6-oxa-östron (12a).
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 1836-1869 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Syntheses of Biscationic, Trypanocidal 1-Benzofuran Compounds2-Phenyl-1-benzofurans with the substituents Br, NO2, CN, and -NH2, -NH-C(=NH)-NH2, -C(=NH)-NH2, -C=N-CH2-CH2-NH in 4′,5-position were synthesized.  -  For arylated formamidine derivatives [Ar-N=CH-N(CH3)2] a simple new preparation was found by reacting amine hydrochlorides with dimethylformamide in the presence of cyanamide.  -  Based on 5- or 6-cyano-1-benzofuran-2-carboxylates a series of α,ω-bis(1-benzofuran-2-yl) derivatives with cyano-, amidino-, or imidazolinyl groups in 5- or 6-position was prepared.
    Notes: 2-Phenyl-1-benzofurane mit den Substituenten Br, NO2 sowie CN und -NH2, -NH-C(=NH)-NH2, -C(=NH)-NH2 sowie -C=N-CH2-CH2-NH in 4′,5-Stellung wurden synthetisiert.  -  Für arylierte Formamidin-Derivate [Ar-N=CH-(CH3)2] fand sich in der Umsetzung von Aminhydrochloriden mit Dimethylformamid in Gegenwart von Cyanamid ein einfaches, neues Herstellungsverfahren.  -  Auf der Basis von 5- oder 6-Cyan-1-benzofuran-2-carbonsäureester konnte eine Serie von α,ω-Bis(1-benzofuran-2-yl)-Derivaten mit Cyan- oder Amidino- oder Imidazolinyl-Gruppen in 5- oder 6-Stellung dargestellt werden.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 409-425 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Syntheses of Antimicrobial Biscationic 2-(Phenoxyphenyl)indoles and -1-benzofuransTen 2-(phenoxyphenyl)indoles and four 2-(phenoxyphenyl)-1-benzofurans with terminal amidinium or imidazolinium groups were synthesized in respect to growth inhibiting properties.
    Notes: Zehn 2-(phenoxyphenyl)indole und vier 2-(Phenoxyphenyl)-1-benzofurane mit endständigen Amidinium- oder Imidazolinium-Gruppen wurden im Hinblick auf wachstumshemmende Eigenschaften synthetisiert.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 438-455 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Antileukemic Indolylvinyl-1-benzofurans and -benzo[b]thiophenes2-[2-(Indol-2-yl)vinyl]-1-benzofuran and -benzo[b]thiophene compounds 6-13 and 18-22 with terminal amidinium or imidazolinium groups were synthesized; in their antileukemic activity in mice they surpass the isosteric 2,2′-vinylenebis(1-benzofuran) and -(benzo[b]-thiophene) compounds.
    Notes: 2-[2-(Indol-2-yl)vinyl]-1-benzofuran- und -benzo[b]thiophen-Verbindungen 6-13 und 18-22 mit endständigen Amidinium- oder Imidazolinium-Gruppen wurden synthetisiert; in ihrer antileukämischen Wirksamkeit übertreffen sie bei der Maus die isosteren 2,2′-Vinylenbis(1-benzofuran)- und -(benzo[b]thiophen)-Verbindungen.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
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  • 8
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 2164-2178 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Syntheses of Antileukemic (Indolylvinyl)indolesThe dinitrile 8a with the skeleton of 2-[(E)-2-(2-indolyl)vinyl]indole is synthesized by various routes; by a simple procedure [(6-cyano-2-indolyl)methyl]- and [(5-cyano-2-indolyl)methyl]triphenylphosphonium bromide (4d and 5c) are prepared and with them the dinitriles 8a, 9a, and 10a and further the derived antileukemic imidazolinyl compounds 8b, 9b, and 10b. With the isomeric skeletons of 6-[(E)-2-(2-indolyl)vinyl]indole and of 6-[(E)-2-(6-indolyl)vinyl]indole the imidazolinyl compounds 18b and 19b are synthesized.
    Notes: Das Dinitril 8a mit dem Gerüst des 2-[(E)-2-(2-Indolyl)vinyl]indols wird auf verschiedenen Wegen synthetisiert; in einfacher Verfahrensweise werden [(6-Cyan-2-indolyl)methyl]- und [(5-Cyan-2-indolyl)methyl]triphenylphosphoniumbromid (4d und 5c) dargestellt und mit ihnen die Dinitrile 8a 9a und 10a sowie ferner die zugehörigen, antileukämischen Imidazolinyl-Verbindungen 8b, 9b und 10b. Mit den isomeren Gerüsten des 6-[(E)-2-(2-Indolyl)-vinyl]indols und des 6-[(E)-2-(6-Indolyl)vinyl]indols werden die Imidazolinyl-Verbindungen 18b und 19b synthetisiert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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  • 9
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 605 (1957), S. 146-157 
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Der Weg einer Khellin-Synthese wird mitgeteilt, bei welcher das bisher unbekannte 4.7-Dimethoxy-6-hydroxy-cumaron mit β-Chlor-crotonsäure-methylester veräthert und die Säure des erhaltenen Äthers zum Khellin ringgeschlossen wird.
    Type of Medium: Electronic Resource
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  • 10
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 612 (1958), S. 34-54 
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Aus dem Extrakt von acetongetrocknetem Fliegenpulver wird bei pH 4.5 Acetataktivierendes Enzym denaturiert ausgefällt. Aus der Restlösung läßt sich bei pH 6.8 durch Ammonsulfat die Cholinacetylase in demselben Konzentrationsbereich fällen wie die bisher bekannten Cholinacetylasen aus Nervengeweben. Bei höheren Konzentrationen fällt eine Phosphotransacetylase, welche Acetylphosphat in Abwesenheit von Coenzym A spaltet und keine Arsenolyse zeigt.  -  An Hand einer entwicklungsgeschichtlichen Zusammenstellung bekannter Vorkommen von Phosphotransacetylasen und Cholinacetylase werden weitere mögliche Vorkommen diskutiert.
    Additional Material: 25 Tab.
    Type of Medium: Electronic Resource
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