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. The preparation of the enantiopure terminal alkyne derivative is based on Trost desymmetrisation, Brown alkoxyallylation and the efficient Colvin reaction. Biological evaluation of the obtained compounds evidenced a promising efficacy in reducing the ability of MDA-MB-361 cell line to migrate.
Synthesis and Biological Evaluation of Migrastatin Macrotriazoles / Passarella, Daniele; Rastelli, Giulio; Murphy, Paul V; Robakiewicz, Stefania; Taciak, Bortlomej; Ulewicz, Katarzyna; Broggini, Gianluigi; Krol, Magdalena; Gabba, Adele. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - ELETTRONICO. - 2017:1(2017), pp. 60-69. [10.1002/ejoc.201600988]
Synthesis and Biological Evaluation of Migrastatin Macrotriazoles
RASTELLI, Giulio;
2017
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. The preparation of the enantiopure terminal alkyne derivative is based on Trost desymmetrisation, Brown alkoxyallylation and the efficient Colvin reaction. Biological evaluation of the obtained compounds evidenced a promising efficacy in reducing the ability of MDA-MB-361 cell line to migrate.
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