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 alkoxyallylation 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.

Synthesis and Biological Evaluation of Migrastatin Macrotriazoles / D. Passarella, G. Rastelli, P.V. Murphy, S. Robakiewicz, B. Taciak, K. Ulewicz, G. Broggini, M. Krol, A. Gabba. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2017:1(2017), pp. 60-69. [10.1002/ejoc.201600988]

Synthesis and Biological Evaluation of Migrastatin Macrotriazoles

D. Passarella
Primo
;
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 reactions. The enantiopure terminal alkyne derivatives were prepared by using the Trost desymmetrization, Brown alkoxyallylation 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.
Bioisosteres; Biological activity; Click chemistry; Macrocycles; Nitrogen heterocycles; Triazoles
Settore CHIM/06 - Chimica Organica
Settore CHIM/08 - Chimica Farmaceutica
2017
5-dic-2016
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/452404
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