| |  Online-Ressource |
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| Verfasst von: | Seehafer, Kai [VerfasserIn]  |
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| | Rominger, Frank [VerfasserIn] |
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| | Helmchen, Günter [VerfasserIn] |
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| | Langhans, Markus [VerfasserIn] |
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| | Robinson, David G. [VerfasserIn] |
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| | Özata, Başak [VerfasserIn] |
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| | Brügger, Britta [VerfasserIn] |
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| | Klein, Christian D. [VerfasserIn] |
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| Titel: | Synthesis and biological properties of novel brefeldin a analogues |
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| Verf.angabe: | Kai Seehafer, Frank Rominger, Günter Helmchen, Markus Langhans, David G.Robinson, Başak Özata, Britta Brügger, Jeroen R.P.M. Strating, Frank J.M. van Kuppeveld, and Christian D.Klein |
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| Umfang: | 13 S. |
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| Fussnoten: | Gesehen am 11.05.2017 |
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| Titel Quelle: | Enthalten in: Journal of medicinal chemistry |
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| Jahr Quelle: | 2013 |
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| Band/Heft Quelle: | 56(2013), 14, S. 5872-5884 |
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| ISSN Quelle: | 1520-4804 |
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| Abstract: | New brefeldin A (1) analogues were obtained by introducing a variety of substituents at C15. Most of the analogues exhibited significant biological activity. (15R)-Trifluoromethyl-nor-brefeldin A (3), (15R)-vinyl-nor-brefeldin A (5), their epimers 4 and 6 as well as (15S)-ethyl-nor-brefeldin A (2) were prepared from the key building blocks 12 or 24 by Julia-Kocienski olefination with tetrazolyl sulfones and subsequent macrolactonization. The vinyl derivative 5 allowed analogues to be synthesized by hydroboration and Suzuki-Miyaura coupling. The following biological properties were assessed: (a) inhibition of cell growth of human cancer cells (NCI), (b) induction of morphological changes of the Golgi apparatus of plant and mammalian cells, and (c) influence on the replication of the enterovirus CVB3. Furthermore, conformational aspects were studied by X-ray crystal structure analysis and molecular mechanics calculations, including docking of the analogues into the brefeldin A binding site of an Arf1/Sec7-complex. |
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| DOI: | doi:10.1021/jm400615g |
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| URL: | Bitte beachten Sie: Dies ist ein Bibliographieeintrag. Ein Volltextzugriff für Mitglieder der Universität besteht hier nur, falls für die entsprechende Zeitschrift/den entsprechenden Sammelband ein Abonnement besteht oder es sich um einen OpenAccess-Titel handelt.
Verlag: http://dx.doi.org/10.1021/jm400615g |
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| | DOI: https://doi.org/10.1021/jm400615g |
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| Datenträger: | Online-Ressource |
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| Sprache: | eng |
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| K10plus-PPN: | 1558501207 |
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| Verknüpfungen: | → Zeitschrift |
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Synthesis and biological properties of novel brefeldin a analogues / Seehafer, Kai [VerfasserIn] (Online-Ressource)
