Synthesis and biological profiling of parthenolide ether analogs
Robert R A Freund1, Philipp Gobrecht2, Pascal Moser1
1Institut für Organische Chemie und Makromolekulare Chemie, Friedrich-Schiller-Universität, Humboldtstr. 10, 07743 Jena, Germany. hd.arndt@uni-jena.de.
Abstract:
Parthenolide (PTL) strongly inhibits the detyrosination of microtubules and accelerates neuronal growth. In order to access cyclic ether derivatives of PTL, ring-closing metathesis (RCM) was investigated in comparison to intramolecular sulfone alkylation. Incompatibility of RCM with epoxides was found in this setting. Biological evaluation for tubulin carboxypeptidase inhibition indicated that the epoxide is crucial for parthenolide's activity.
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