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ISBN 9783843903721

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978-3-8439-0372-1, Reihe Organische Chemie

Aroonchai Saiai
Stereoselective Total Synthesis and Biological Evaluation of Arene-Cr(CO)3 Complexes as Potential Bioactive Compounds

212 Seiten, Dissertation Universität Köln (2012), Softcover, A5

Zusammenfassung / Abstract

Recently, we reported on AKS-01, a hydrophenalene-Cr(CO)3 complex structurally related to the pseudopterosins, a class of natural products showing significant and specific NOD2 inhibiting activities causing the decrease in inflammatory response. Therefore, the syntheses of AKS-01 derivatives are important for further studies of the biological activity including structure activity relationships.

Additionally, we decided to introduce the Cr(CO)3 moiety to chalcones in order to improve the biological activity. In the course of the present work a library of AKS-01 analogs was successfully synthesized through diastereoselective benzylic deprotonation, alkylation and subsequent SmI2-mediated cyclization. We could also derivatize the final products by either introducing different benzyloxy substituents or modifying the side chain by alkylation and olefin cross metathesis. The investigation of NOD2 inhibiting activities of AKS-01 analogs showed promising results. Complex 104b proved to be the most active in selective NOD2 inhibition.

The chalcone-Cr(CO)3 analogs were synthesized by palladium-catalyzed carbonylative cross-coupling Suzuki reaction between chloroarene-Cr(CO)3 complexes and various trans-2-arylvinylboronic acids in high yield.