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  • 1970-1974  (6)
  • 1
    Electronic Resource
    Electronic Resource
    Chromane, XVIII Synthese von 7α-Methyl-6-oxa-östron (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 3313-3328 
    Details
    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
    URL: http://dx.doi.org/10.1002/cber.19711041035
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  • 2
    Electronic Resource
    Electronic Resource
    Trypanocide Diamidine mit drei Ringen in zwei isolierten Ringsystemen (1972)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 760 (1972), S. 37-87 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Trypanocidal Diamidines with Three Rings in Two Isolated Ring SystemsDiamidines are synthesized, which are derived of type A of 6- or 5-amidino-2-[4-amidino-phenyl]-thionaphthene or -benzofuran by further variation of the condensed five-membered ring, by insertion of a bridge of one or two atoms between the two ring systems and by variation of the amidino groups. - Only 5-amidino-2-[4-amidinophenyl]-indazole (4c) and -benztriazole (10d) retained the outstanding trypanocidal properties of type A.
    Notes: Es werden Diamidine synthetisiert, welche sich vom Typ A des 6- oder 5-Amidino-2-[4-amidino-phenyl]-thionaphthens oder -benzofurans dadurch ableiten, daß der annelierte Fünfring weiter variiert wird, daß ein- und zweigliedrige Brücken zwischen die beiden Ringsysteme eingeschoben werden, und daß die flankierenden Amidino-Gruppen abgewandelt werden. - Nur bei 5-Amidino-2-[4-amidino-phenyl]-indazol (4c) und -benztriazol (10d) bleiben die hervorragenden trypanociden Eigenschaften des Typs A erhalten.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.19727600105
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  • 3
    Electronic Resource
    Electronic Resource
    Trypanocide Diamidine des 2-Phenyl-benzofurans, 2-Phenyl-indens und 2-Phenyl-indols (1971)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 749 (1971), S. 68-89 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Trypanocide Diamidines of 2-Phenylbenzofuran, 2-Phenylindene and 2-PhenylindoleDiamidines with the amidino-groups in 4′.5- and 4′.6-position of the ring skeletons of 2-phenylbenzofuran (4e, 5e, 3e), of 2-phenylindene (10d, 16a, 16b, 16c, 16d), of 2-phenyl-2.3-dihydroindene (17b) and of 2-phenylindole (18l, 18n, 18p, 19d, 19e) are synthesized; the 3′.5- and 3′.6-diamidines 18m, 18o of 2-phenylindole are also prepared. - The activity of 4′.5-diamidine 4e of 2-phenylbenzofuran against Trypanosoma rhodesiense surpasses all others. The spectrum of activity of diamidines of 2-phenylindene resembles that of the diamidines of 2-phenylthionaphthene with the main activity against T. gambiense. The 4′.6-diamidine 18n of 2-phenylindole exhibits the highest and rarely found activity against T. congolense.
    Notes: Es werden Diamidine synthetisiert, welche die Amidino-Gruppen in 4′.5- bzw. 4′.6-Stellung der Ringgerüste des 2-Phenyl-benzofurans (4e, 5e und 3e), des 2-Phenyl-indens (10d, 16a, 16b, 16c, 16d), des 2-Phenyl-2.3-dihydro-indens (17b) sowie des 2-Phenyl-indols (18l, 18n, 18p, 19d, 19e) enthalten; von letzterem werden außerdem die 3′.5- bzw. 3′.6-Diamidine (18m bzw. 18o) dargestellt. - Das 4′.5-Diamidin 4e des 2-Phenyl-benzofurans besitzt eine überragende Wirksamkeit gegen Trypanosoma rhodesiense. Die Diamidine des 2-Phenylindens haben ein Wirkungsspektrum wie jene des 2-Phenyl-thionaphthens mit dem Schwerpunkt gegen T. gambiense, und das 4′.6-Diamidin 18n des 2-Phenyl-indols besitzt eine überragende, seltene Wirksamkeit gegen T. congolense.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.19717490110
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  • 4
    Electronic Resource
    Electronic Resource
    Trypanocide Diamidine mit vier Ringen in einem oder zwei Ringsystemen (1973)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1973 (1973), S. 1112-1140 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Trypanocidal Diamidines with Four Rings in One or Two Ring SystemsThe trypanocidal properties of diamidines of type A are diminished by rigidity of the skeleton and by its enlargement, as was shown by preparation of diamidines with the following skeletons: 10H-[1]benzothieno[3,2-b]indole (1c); chrysene (4g); cis-4b,5,6,10b,11,12-hexa-hydrochrysene (8g); 2-(2-benzofuranyl)indole (10c, 11c); 2-naphthylbenzo[b]thiophene (12d), 1-phenylnaphtho[2,1-b]thiophene (18c); bis(2-benzofuranyl)-methane (24d), -ethylenes (25c, 28c, 31c) and -ethanes (29b, 30b).
    Notes: Die trypanociden Eigenschaften der Diamidine vom Typ A werden durch Starrheit des Molekülgerüstes und durch seine Flächenvergrößerung beeinträchtigt, wie sich durch die Darstellung von Diamidinen mit folgenden Gerüsten zeigen ließ: 10H-[1]Benzothieno-[3,2-b]indol (1c); Chrysen (4g); cis-4b,5,6,10b,11,12-Hexahydrochrysen (8g); 2-(2-Benzofuranyl)indol (10c, 11c); 2-Naphthylbenzo[b]thiophen (12d); 1-Phenylnaphtho[2,1-b]thiophen (18c); Bis(2-benzofuranyl)-methan (24d), -äthylene (25c, 28c, 31c) und -äthane (29b, 30b).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197319730708
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  • 5
    Electronic Resource
    Electronic Resource
    Gegen Malaria wirksame 6-Aminochinoline, II. 6-[ω-Diäthylamino-alkylamino]- und 6-[ω-Amino-alkylamino]-5.8-dimethoxy-chinaldine (1971)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 744 (1971), S. 119-128 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Antimalarial 6-Aminoquinolines, II. 6-[ω-Diethylaminoalkylamino]- and 6-[ω-Aminoalkyl-amino]-5,8-dimethoxyquinaldinesTwelve derivatives of 6-amino-5,8-dimethoxyquinaldine with the basic side chains (C2H5)2N—(CH2)n—NH (n = 2, 3; 15, 16) and H2N—(CH2)n—CHR—NH— (n = 1 - 9, R = H, CH3; 21a-k) in the 6-position are prepared with the aim of studying the influence of the basic side chain on malarial activity and toxicity of the 6-aminoquinolines.
    Notes: Zwölf in 6-Stellung basisch alkylierte 6-Amino-5.8-dimethoxy-chinaldine mit den Seiten-ketten (C2H5)2N—(CH2)n—NH— (n = 2, 3; 15, 16) und H2N—(CH2)n—CHR—NH—(n = 1—9, R = H, CH3; 21a-k) wurden synthetisiert, um den Einfluß der basischen Seitenkette auf Malaria-Wirksamkeit und Toxizität der 6-Amino-chinoline zu untersuchen.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.19717440115
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  • 6
    Electronic Resource
    Electronic Resource
    Mehrkernige Thiophene, VIII1) Trypanocide Diamidine des 2-Phenyl-thionaphthens (1970)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 734 (1970), S. 23-45 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Polynuclear Thiophenes, VIII1). Trypanocidal Diamidines of 2-Phenyl-thionaphtheneThe diamidines of 2-phenyl-thionaphthene with the amidino groups in the positions 4′, 6 (7), 4′,5 (19e), 3′.6 (12g) and 3′,5 (14g) are synthesized. The 1.1-dioxides 20b and 22b of the 4′,6-and of the 4′,5-diamidines are also prepared as well as the corresponding 1,1-dioxides hydrogenated in 2,3-position (21b, 23b). - Both the 4′,6- and the 4′,5-diamidine exhibit in mice a general and outstanding trypanocidal activity which culminates for the 4′,6-compound 7 in the highest activity against T. gambiense.
    Notes: Die Diamidine des 2-Phenyl-thionaphthens mit den Amidinogruppen in 4′.6-(7), 4′.5-(19e), 3′.6-(12g) und 3′.5-Stellung (14g) werden synthetisiert. Vom 4′.6- und vom 4′.5-Diamidin werden die 1.1-Dioxide (20b, 22b) sowie deren 2.3-Dihydro-Derivate (21b, 23b) hergestellt. - Das 4′.6- und das 4′.5-Diamidin zeigen im Mäuseversuch ein ausgezeichnetes trypanocides Wirkungsspektrum (Tab. 1), worin die 4′.6-Verbindung 7 die höchste Wirksamkeit gegen T. gambiense aufweist.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.19707340104
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