Synthesis and Characterization of a Click-Assembled 18-Atom Macrocycle That Displays Selective AXL Kinase Inhibitory Activity

[Image: see text] A novel macrocyclic construct consisting of a pyrazolopyrimidine scaffold concatenated to a benzene ring through two triazoles has been developed to investigate uncharted chemical space with bioactive potential. The 18-atom macrocycle was assembled via a double copper-catalyzed alk...

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Autores principales: Cruz-López, Olga, Temps, Carolin, Longo, Beatrice, Myers, Samuel H., Franco-Montalban, Francisco, Unciti-Broceta, Asier
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6921642/
https://www.ncbi.nlm.nih.gov/pubmed/31867559
http://dx.doi.org/10.1021/acsomega.9b03525
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author Cruz-López, Olga
Temps, Carolin
Longo, Beatrice
Myers, Samuel H.
Franco-Montalban, Francisco
Unciti-Broceta, Asier
author_facet Cruz-López, Olga
Temps, Carolin
Longo, Beatrice
Myers, Samuel H.
Franco-Montalban, Francisco
Unciti-Broceta, Asier
author_sort Cruz-López, Olga
collection PubMed
description [Image: see text] A novel macrocyclic construct consisting of a pyrazolopyrimidine scaffold concatenated to a benzene ring through two triazoles has been developed to investigate uncharted chemical space with bioactive potential. The 18-atom macrocycle was assembled via a double copper-catalyzed alkyne–azide cycloaddition (CuAAC) reaction between 1,3-bis(azidomethyl)benzene and a bis-propargylated pyrazolo[3,4-d]pyrimidine core. The resulting macrocycle was functionalized further into a multicyclic analog that displays selective inhibitory activity against the receptor tyrosine kinase AXL.
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spelling pubmed-69216422019-12-20 Synthesis and Characterization of a Click-Assembled 18-Atom Macrocycle That Displays Selective AXL Kinase Inhibitory Activity Cruz-López, Olga Temps, Carolin Longo, Beatrice Myers, Samuel H. Franco-Montalban, Francisco Unciti-Broceta, Asier ACS Omega [Image: see text] A novel macrocyclic construct consisting of a pyrazolopyrimidine scaffold concatenated to a benzene ring through two triazoles has been developed to investigate uncharted chemical space with bioactive potential. The 18-atom macrocycle was assembled via a double copper-catalyzed alkyne–azide cycloaddition (CuAAC) reaction between 1,3-bis(azidomethyl)benzene and a bis-propargylated pyrazolo[3,4-d]pyrimidine core. The resulting macrocycle was functionalized further into a multicyclic analog that displays selective inhibitory activity against the receptor tyrosine kinase AXL. American Chemical Society 2019-12-03 /pmc/articles/PMC6921642/ /pubmed/31867559 http://dx.doi.org/10.1021/acsomega.9b03525 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Cruz-López, Olga
Temps, Carolin
Longo, Beatrice
Myers, Samuel H.
Franco-Montalban, Francisco
Unciti-Broceta, Asier
Synthesis and Characterization of a Click-Assembled 18-Atom Macrocycle That Displays Selective AXL Kinase Inhibitory Activity
title Synthesis and Characterization of a Click-Assembled 18-Atom Macrocycle That Displays Selective AXL Kinase Inhibitory Activity
title_full Synthesis and Characterization of a Click-Assembled 18-Atom Macrocycle That Displays Selective AXL Kinase Inhibitory Activity
title_fullStr Synthesis and Characterization of a Click-Assembled 18-Atom Macrocycle That Displays Selective AXL Kinase Inhibitory Activity
title_full_unstemmed Synthesis and Characterization of a Click-Assembled 18-Atom Macrocycle That Displays Selective AXL Kinase Inhibitory Activity
title_short Synthesis and Characterization of a Click-Assembled 18-Atom Macrocycle That Displays Selective AXL Kinase Inhibitory Activity
title_sort synthesis and characterization of a click-assembled 18-atom macrocycle that displays selective axl kinase inhibitory activity
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6921642/
https://www.ncbi.nlm.nih.gov/pubmed/31867559
http://dx.doi.org/10.1021/acsomega.9b03525
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