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  • 1
    Electronic Resource
    Electronic Resource
    Diethylstilbestrol-linked cytotoxic agents. Synthesis and binding affinity for estrogen receptors (1989)
    s.l. : American Chemical Society
    Journal of medicinal chemistry 32 (1989), S. 1532-1538 
    Details
    ISSN: 1520-4804
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/jm00127a022
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  • 2
    Electronic Resource
    Electronic Resource
    Hexestrol-linked cytotoxic agents: synthesis and binding affinity for estrogen receptors (1989)
    s.l. : American Chemical Society
    Journal of medicinal chemistry 32 (1989), S. 1538-1547 
    Details
    ISSN: 1520-4804
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/jm00127a023
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  • 3
    Electronic Resource
    Electronic Resource
    A new synthesis of ortho-Quinones by transition-metal-mediated oxygenation of phenols with tert-butylhydroperoxide and the mimoun oxodiperoxo molybdenum complex [Mo(O2)2O] · Py · HMPT (1989)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 122 (1989), S. 2323-2330 
    Details
    ISSN: 0009-2940
    Keywords: ortho-Quinones ; tert-Butyl hydroperoxide ; Phenols, oxygenation ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Eine neue ortho-Chinon-Synthese durch Oxygenierung von Phenolen mit den Systemen tert-Butylhydroperoxid/Übergangsmetall-Komplex und dem Mimounschen Oxodiperoxo-Molydbän-Komplex [Mo(O2)2O] · py · HMPTPhenole können mit einer Kombination der Übergangsmetall-Komplexe Ti(OiPr)4, VO(acac)2, Zr(acac)4, Zr(OnPr)4 und tert-Butylhydroperoxid oder mit [Mo(O2)2O] · Py · HMPT spezifisch zu ortho-Chinonen oxygeniert werden. Naphthole, Anthracenole, Phenanthrole und Donor-substituierte einkernige Phenole werden glatt in die entsprechenden 1,2-Chinone übergeführt. Ungehinderte ortho-Napthochinone können unter Michael-Addition mit nicht umgesetztem Ausgangsmaterial zu Biarylen abreagieren.
    Notes: A specific oxygenation of phenols to ortho-quinones can be effected by a combination of the transition metal complexes Ti(OiPr)4, VO(acac)2, Zr(acac)4, Zr(OnPr)4 and tert-butylhydroperoxide (TBHP) or [Mo(O2)2O] · Py · HMPT. Naphthols, anthracenols, phenanthrols and donor substituted mononuclear phenols are readily converted into the corresponding 1,2-quinones. Unhindered ortho-naphthoquinones can yield binaphthyls with unreacted starting material by Michael addition.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19891221220
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  • 4
    Electronic Resource
    Electronic Resource
    Simple Synthesis of Anthracyclinones by Cyclization of an Intermediate HydroxynitronateSynthetic Anthracyclinones, Part 30.-Part 29: [1] (1986)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 25 (1986), S. 339-340 
    Details
    ISSN: 0570-0833
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: No. Abstract.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.198603391
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  • 5
    Electronic Resource
    Electronic Resource
    Total Synthesis of Anthracyclinone [New Synthetic Methods (60)]Dedicated to Professor Albert Mondon on the occasion of his 70th birthday (1986)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 25 (1986), S. 790-807 
    Details
    ISSN: 0570-0833
    Keywords: Anthracyclinones ; Synthetic methods ; Antibiotics ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The remarkable antitumor properties of anthracycline antibiotics have motivated synthetic chemists, and a large number of groups have been active recently in this field. Initially, there was very little hope for this class of substances due to their extreme toxicity. However, the dividing line between toxicity and desired pharmacological effect has broadened to such an extent, partly through microbiological methods (new strains, mutants) and partly through semisynthetic modifications, that today anthracyclines take number one place (over 20% of the market) in the chemotherapy of (human) cancer. The demands made on modern cytostatica are extremely high, as may be seen from the fact that of the more than 600000 drugs tested in animals, only about 40 are in clinical use. In the meantime, some anthracyclines obtained by total synthesis are also in clinical testing. In this review it will hopefully be demonstrated that all those concerned in the chemotherapeutic use of these substances have also contributed to the general progress made in the solution of regio- and stereo-chemical problems of linearly annelated ring systems.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.198607901
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  • 6
    Electronic Resource
    Electronic Resource
    Einfache Anthracyclinon-Synthese durch Cyclisierung eines intermediären HydroxynitronatsSynthetische Anthracyclinone, 30. Mitteilung. - 29. Mitteilung: [1]. (1986)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 98 (1986), S. 338-339 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19860980409
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  • 7
    Electronic Resource
    Electronic Resource
    Totalsynthese von AnthracyclinonenProfessor Albert Mondon zum 70. Geburtstag gewidmet (1986)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 98 (1986), S. 788-805 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Die bemerkenswerten Antitumor-Eigenschaften der Anthracyclin-Antibiotica haben auch die Synthesechemiker auf den Plan gerufen und in den letzten Jahren zu intensiver Aktivität auf diesem Gebiet geführt. Wegen der oft extremen Toxizität wurden der Substanzklasse ursprünglich wenig Chancen eingeräumt. Es gelang aber, teils durch mikrobielle Methoden (neue Stämme, Mutanten), teils durch halbsynthetische Modifikationen, den schmalen Grat zwischen Toxizität und gewünschter Wirkung so zu verbreitern, daß die Anthracycline heute den ersten Platz bei der Behandlung von Krebserkrankungen einnehmen (über 20% Marktanteil). Wie hoch dabei die Anforderungen an moderne Cytostatica sind, zeigt die Tatsache, daß von über 600000 seit 1955 im Tiermodell getesteten Substanzen nur ca. 40 den Weg in die Klinik geschafft haben. Im klinischen Test befinden sich inzwischen auch einige totalsynthetische Anthracycline. Daß die Beschäftigung der Synthesechemie mit dieser Substanzklasse darüber hinaus auch allgemeine Fortschritte bei der Lösung regio- und stereochemischer Probleme linear anellierter Ringsysteme gebracht hat, wird diese Übersicht zeigen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19860980904
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  • 8
    Electronic Resource
    Electronic Resource
    Synthetische Anthracyclinone, XXXIV. Ein enantiomerenreiner AB-Baustein zur Daunomycinon-Synthese unter Einbau von (S)-Äpfelsäure (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 515-520 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthetic Anthracyclinones, XXXIV. - An Enantiomerically Pure AB Building Block for a Daunomycinone Synthesis via Incorporation of (S)-Malic Acid(S)-Malic acid (1) is incorporated via the dilithium salt 4 of the acetal 3 into the fully functionalized daunomycinone building block 24 without loss of enantiomeric purity.
    Notes: (S)-Äpfelsäure (1) wird über das Dilithiumsalz 4 des Acetals 3 ohne Verlust der Enantiomerenreinheit in den vollständig funktionalisierten Daunomycinon-Baustein 24 eingebaut.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870367
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  • 9
    Electronic Resource
    Electronic Resource
    Synthetische Anthracyclinone, 35. Synthese des Nogalamycin-Aglycons (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 1037-1043 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthetic Anthracyclinones, 35. - Synthesis of the Nogalamycin AglyconThe keto ester 13 is predominantly cyclized to the 1,2-cis-hydroxy ester 16 under aprotic conditions. Dimethyl ether 16 is split to 17. Hydroxylation of 17 by bromination and hydrolysis affords the nogalamycin aglycon 19 with 2,4-trans-hydroxy groups.
    Notes: Der Ketoester 13 cyclisiert unter aprotischen Bedingungen bevorzugt zum 1,2-cis-Hydroxyester 16, der zu 17 gespalten wird. Hydroxylierung von 17 durch Bromierung und Solvolyse führt zum Nogalamycin-Aglycon 19 mit 2,4-trans-Hydroxygruppen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870870
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  • 10
    Electronic Resource
    Electronic Resource
    Synthetic Anthracyclinones, 37. Total synthesis of (+)-β-rhodomycinone, (+)-1-deoxy-β-rhodomycinone, and (+)-1-deoxy-γ-rhodomycinone by incorporation of (S)-α-hydroxybutyric acid (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 949-953 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthetische Anthracyclinone, 37. - Totalsynthese von (+)-β-Rhodomycinon, (+)-1-Desoxy-β-rhodomycinon und (+)-1-Desoxy-γ-rhodomycinon durch Einbau von (S)-α-HydroxybuttersäureBeide Enantiomere des optisch aktiven Bausteins 4 für die Anthracyclinon-Synthese wurden ausgehend von der α-Hydroxybuttersäure 7 hergestellt. Schlüsselschritte waren die diastereoselektive Alkylierung von 5 zu 8 gefolgt von DIBAH-Reduktion und Umacetalisierung zu 10. Die Kupplung von 4 an Chinizarin (11) und 1,4,5-Trihydroxyanthrachinon (3) durch zwei aufeinanderfolgende Marschalk Reaktionen und die Hydroxylierung der Benzylstellung lieferte den Naturstoff (+)-β-Rhodomycinon (18) und (+)-1-Desoxy-β-rhodomycinon (17).
    Notes: Both enantiomers of the optically active building block 4 for anthracyclinone synthesis have been prepared from α-hydroxybutyric acid 7. Key steps were the diastereoselective alkylation of the acetal 5 to 8 followed by DIBAH reduction and transacetalization to 10. Coupling of 4 to quinizarine (11) and 1,4,5-trihydroxy-9,10-anthraquinone (3) by two successive Marschalk reactions and benzylic hydroxylation afforded the natural product (+)-β-rhodomycinone (18) and (+)-1-deoxy-β-rhodomycinone (17).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819881003
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