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Synthesis and Biological Evaluation of Migrastatin Macrotriazoles
Author(s) -
Gabba Adele,
Robakiewicz Stefania,
Taciak Bartłomiej,
Ulewicz Katarzyna,
Broggini Gianluigi,
Rastelli Giulio,
Krol Magadalena,
Murphy Paul V.,
Passarella Daniele
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600988
Subject(s) - chemistry , alkyne , desymmetrization , enantiopure drug , cycloaddition , azide , combinatorial chemistry , click chemistry , organic chemistry , catalysis , enantioselective synthesis
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.