Synthesis and Biological Evaluation of Migrastatin Macrotriazoles

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

doi:10.1002/ejoc.201600988

Synthesis and Biological Evaluation of Migrastatin Macrotriazoles

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

Infectious Disease

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

16 Citations (Scopus)

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.

Original language	English
Pages (from-to)	60-69
Number of pages	10
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	1
DOIs	https://doi.org/10.1002/ejoc.201600988
Publication status	Published - 3 Jan 2017

Keywords

Bioisosteres
Biological activity
Click chemistry
Macrocycles
Nitrogen heterocycles
Triazoles

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10.1002/ejoc.201600988

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title = "Synthesis and Biological Evaluation of Migrastatin Macrotriazoles",

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.",

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T1 - Synthesis and Biological Evaluation of Migrastatin Macrotriazoles

AU - Gabba, Adele

AU - Robakiewicz, Stefania

AU - Taciak, Bartłomiej

AU - Ulewicz, Katarzyna

AU - Broggini, Gianluigi

AU - Rastelli, Giulio

AU - Krol, Magadalena

AU - Murphy, Paul V.

AU - Passarella, Daniele

PY - 2017/1/3

Y1 - 2017/1/3

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AB - 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.

KW - Bioisosteres

KW - Biological activity

KW - Click chemistry

KW - Macrocycles

KW - Nitrogen heterocycles

KW - Triazoles

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DO - 10.1002/ejoc.201600988

M3 - Article

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SP - 60

EP - 69

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 1

ER -

Synthesis and Biological Evaluation of Migrastatin Macrotriazoles

Abstract

Keywords

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