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Neuartige Cannabinoide -- Synthese Und Biologische Evaluierung

Neuartige Cannabinoide -- Synthese Und Biologische Evaluierung

          
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About the Book

Cannabinoide Rezeptoren sind vielversprechende Wirkstofftargets zur Behandlung der Symptome von AIDS, Krebs und Multipler Sklerose, weswegen der Entwicklung moderner Cannabinoide und der Erforschung ihrer Rezeptoren eine hohe Bedeutung zukommt. In dieser Arbeit gelang die Synthese zahlreicher neuer 3-Benzylcumarine mit Hilfe der de novo-Strategie von Brase et al. unter Verwendung einer NHC-unterstutzten Umpolungsreaktion. Die entstandene Wirkstoffbibliothek wurde einer Structure-Activity-Relationship-Studie unterzogen, deren biologische Evaluierung eine selektive und hohe Affinitat gegenuber cannabinoiden Rezeptoren, wie CB1-, CB2- und GPR55, mit Ki- und IC50-Werten im nanomolaren Bereich ergab, wobei insbesondere fur GPR55-Antagonisten ein neues Leitstrukturmodell aufgestellt werden konnte. Zudem wurden erstmals unterschiedliche Cannabinoid-Liganden in Form von polaritatssensitiven 3-Hydroxychromon-Farbstoffen synthetisiert mit dem Ziel der Integration des Fluorophors im Pharmakophor. Diese Liganden wurden sowohl eine Visualisierung der cannabinoiden Rezeptoren als auch die detaillierte Untersuchung der Mikroumgebung der spezifischen Bindungsstelle am Rezeptor bezuglich der Polaritat ermoglichen. Im Zuge der formalen Syntheseroute von Tetrahydrocannabinol - dem dritten Teil dieser Arbeit - konnte zum einen 1-Methoxy-9-demethyl-THC erfolgreich isoliert werden, zum anderen lasst der modulare Aufbau des cannabinoidtypischen Tricyclus auch den synthetischen Zugang weiterer Cannabinoid-Derivate wie beispielsweise Nabilon zu.


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Product Details
  • ISBN-13: 9783832538125
  • Publisher: Logos Verlag Berlin
  • Binding: Paperback
  • Language: German
  • Returnable: N
  • Spine Width: 0 mm
  • Width: 145 mm
  • ISBN-10: 3832538127
  • Publisher Date: 30 Oct 2014
  • Height: 210 mm
  • No of Pages: 224
  • Series Title: Beitrage Zur Organischen Synthese
  • Weight: 700 gr


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