Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development

[Image: see text] The bioderived platform molecule levoglucosenone (LGO, 1) and its readily prepared pseudoenantiomer (iso-LGO, 2) have each been subjected to α-iodination reactions with the product halides then being engaged in palladium-catalyzed Ullmann cross-coupling reactions with various bromo...

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Autores principales: Liu, Xin, Carr, Paul, Gardiner, Michael G., Banwell, Martin G., Elbanna, Ahmed H., Khalil, Zeinab G., Capon, Robert J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7301580/
https://www.ncbi.nlm.nih.gov/pubmed/32566859
http://dx.doi.org/10.1021/acsomega.0c01331
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author Liu, Xin
Carr, Paul
Gardiner, Michael G.
Banwell, Martin G.
Elbanna, Ahmed H.
Khalil, Zeinab G.
Capon, Robert J.
author_facet Liu, Xin
Carr, Paul
Gardiner, Michael G.
Banwell, Martin G.
Elbanna, Ahmed H.
Khalil, Zeinab G.
Capon, Robert J.
author_sort Liu, Xin
collection PubMed
description [Image: see text] The bioderived platform molecule levoglucosenone (LGO, 1) and its readily prepared pseudoenantiomer (iso-LGO, 2) have each been subjected to α-iodination reactions with the product halides then being engaged in palladium-catalyzed Ullmann cross-coupling reactions with various bromonitropyridines. The corresponding α-pyridinylated derivatives such as 11 and 24, respectively, are produced as a result. Biological screening of such products reveals that certain of them display potent and selective antimicrobial and/or cytotoxic properties. In contrast, the azaindoles obtained by reductive cyclization of compounds such as 11 and 12 are essentially inactive in these respects. Preliminary mode-of-action studies are reported.
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spelling pubmed-73015802020-06-19 Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development Liu, Xin Carr, Paul Gardiner, Michael G. Banwell, Martin G. Elbanna, Ahmed H. Khalil, Zeinab G. Capon, Robert J. ACS Omega [Image: see text] The bioderived platform molecule levoglucosenone (LGO, 1) and its readily prepared pseudoenantiomer (iso-LGO, 2) have each been subjected to α-iodination reactions with the product halides then being engaged in palladium-catalyzed Ullmann cross-coupling reactions with various bromonitropyridines. The corresponding α-pyridinylated derivatives such as 11 and 24, respectively, are produced as a result. Biological screening of such products reveals that certain of them display potent and selective antimicrobial and/or cytotoxic properties. In contrast, the azaindoles obtained by reductive cyclization of compounds such as 11 and 12 are essentially inactive in these respects. Preliminary mode-of-action studies are reported. American Chemical Society 2020-06-08 /pmc/articles/PMC7301580/ /pubmed/32566859 http://dx.doi.org/10.1021/acsomega.0c01331 Text en Copyright © 2020 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 Liu, Xin
Carr, Paul
Gardiner, Michael G.
Banwell, Martin G.
Elbanna, Ahmed H.
Khalil, Zeinab G.
Capon, Robert J.
Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development
title Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development
title_full Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development
title_fullStr Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development
title_full_unstemmed Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development
title_short Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development
title_sort levoglucosenone and its pseudoenantiomer iso-levoglucosenone as scaffolds for drug discovery and development
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7301580/
https://www.ncbi.nlm.nih.gov/pubmed/32566859
http://dx.doi.org/10.1021/acsomega.0c01331
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