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Synthese Von Ergochromen Und Deren Dimerisierung Zum Aufbau Von Secalonsauren

Synthese Von Ergochromen Und Deren Dimerisierung Zum Aufbau Von Secalonsauren

          
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About the Book

Naturstoffe, die auf einen Xanthenon-Grundgerust basieren, stellen eine beachtliche Klasse von Mykotoxinen dar. Aufgrund ihrer interessanten biologischen Eigenschaften haben insbesondere die Secalonsauren grosses Interesse geweckt. Im Rahmen der vorliegenden Arbeit sollte ein synthetischer Zugang zu den Secalonsauren sowie strukturell verwandten Naturstoffen entwickelt werden. Zunachst wurde eine Syntheseroute fur Blennolid A ausgearbeitet. Da dieser Naturstoff dem Monomer der Secalonsaure B entspricht, wurden zugleich Voraussetzungen fur eine erfolgreiche Totalsynthese von Secalonsauren geschaffen. Hierbei wurde ausgehend von 2-Hydroxy-6-methoxybenzaldehyd und (4S,5R)-4-Hydroxy-5-methyl-2-cyclohexenon zunachst das Tetrahydroxanthenon-Grundgerust in einer Domino-Oxa-Michael-Aldolreaktion aufgebaut. Nach Einfuhrung der erforderlichen funktionellen Gruppen wurde epi-Blennolid A, nachgewiesen durch Massenspektroskopie, erhalten. Die Totalsynthese der Secalonsauren erfordert eine Dimerisierung der Tetrahydroxanthenon-Einheiten. In der vorliegenden Arbeit wurden Methoden wie die phenolische Oxidation und verschiedene Kreuzkupplungsreaktionen untersucht. Die phenolische Kupplung erforderte die Suche nach dem geeigneten Oxidationsmittel und die Modifikation der Struktur des Xanthons. So konnte in Abhangigkeit der Struktur des Xanthons eine Dimerisierung zur Biarylverbindung und zum Diarylether erreicht werden. Ein alternativer Zugang zu dimeren Tetrahydroxanthenonen konnte mittels Kreuzkupplungsreaktion erreicht werden. Im Zuge dieser Arbeit wurden Strukturanaloga der Secalonsauren synthetisiert, die auf biologische Aktivitat untersucht wurden. Durch in vitro Disk Diffusion Assays wurde die toxische Wirkung der Tetrahydroxanthenone auf verschiedene Zelltypen untersucht. Hierbei wurde keine Selektivitat beobachtet, die Substanzen verhielten sich sowohl kranken als auch gesunden Zellen gegenuber toxisch. Weiterhin wurde mit Hilfe des Sulforhodamin B-Tests die wachstumshemmende Wirkung der Tetrahydroxanthenone auf die Colonkarzinomzelllinie HT29 untersucht. Von allen getesteten Substanzen zeigte das unsubstituierte Tetrahydroxanthenon die grosste Potenz hinsichtlich einer Wachstumshemmung von HT29 Zellen.


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Product Details
  • ISBN-13: 9783832523602
  • Publisher: Logos Verlag Berlin
  • Binding: Paperback
  • Language: German
  • Returnable: N
  • Spine Width: 0 mm
  • Width: 145 mm
  • ISBN-10: 383252360X
  • Publisher Date: 31 Dec 2009
  • Height: 210 mm
  • No of Pages: 177
  • Series Title: Beitrage Zur Organischen Synthese
  • Weight: 700 gr


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