Synthesis and biological evaluation of migrastatin macrotriazoles

Gabba, Adele; Robakiewicz, Stefania; Taciak, Bartłomiej; Ulewicz, Katarzyna; Broggini, Gianluigi; Rastelli, Giulio; Krol, Magadalena; Murphy, Paul V.; Passarella, Daniele

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2016-12-05

Author

Gabba, Adele

Robakiewicz, Stefania

Taciak, Bartłomiej

Ulewicz, Katarzyna

Broggini, Gianluigi

Rastelli, Giulio

Krol, Magadalena

Murphy, Paul V.

Passarella, Daniele

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Gabba, Adele; Robakiewicz, Stefania; Taciak, Bartłomiej; Ulewicz, Katarzyna; Broggini, Gianluigi; Rastelli, Giulio; Krol, Magadalena; Murphy, Paul V. Passarella, Daniele (2016). Synthesis and biological evaluation of migrastatin macrotriazoles. European Journal of Organic Chemistry (1), 60-69

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http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201600988/pdf

Abstract

The synthesis of three macrotriazoles that are analogues of migrastatin is reported. The synthesis is based on copper(I)- and ruthenium-catalyzed azide-alkyne cycloaddition reactions. The enantiopure terminal alkyne derivatives were prepared by using the Trost desymmetrization, Brown alkoxy-allylation and an efficient Colvin reaction. Biological evaluation of the products revealed a promising efficiency in reducing the ability of MDA-MB-361 cell lines to migrate.

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http://hdl.handle.net/10379/11569

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