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:10.13025/25797

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

University of Galway
Warsaw University of Life Sciences - SGGW
University of Insubria
University of Modena and Reggio Emilia
University of Milan

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/10.13025/25797 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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10.13025/25797Licence: CC BY-NC-ND
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.",

keywords = "Bioisosteres, Biological activity, Click chemistry, Macrocycles, Nitrogen heterocycles, Triazoles",

author = "Adele Gabba and Stefania Robakiewicz and Bart{\l}omiej Taciak and Katarzyna Ulewicz and Gianluigi Broggini and Giulio Rastelli and Magadalena Krol and Murphy, \{Paul V.\} and Daniele Passarella",

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doi = "10.13025/25797",

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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

N2 - 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.

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

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

UR - https://www.scopus.com/pages/publications/85008255051

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DO - 10.13025/25797

M3 - Article

SN - 1434-193X

VL - 2017

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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