α,α-Difluorophosphonohydroxamic Acid Derivatives among the Best Antibacterial Fosmidomycin Analogues

Three α,α-difluorophosphonate derivatives of fosmidomycin were synthesized from diethyl 1,1-difluorobut-3-enylphosphonate and were evaluated on Escherichia coli. Two of them are among the best 1-deoxy-d-xylulose 5-phosphate reductoisomerase inhibitors, with IC(50) in the nM range, much better than f...

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Autores principales: Dreneau, Aurore, Krebs, Fanny S., Munier, Mathilde, Ngov, Chheng, Tritsch, Denis, Lièvremont, Didier, Rohmer, Michel, Grosdemange-Billiard, Catherine
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8397956/
https://www.ncbi.nlm.nih.gov/pubmed/34443699
http://dx.doi.org/10.3390/molecules26165111
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author Dreneau, Aurore
Krebs, Fanny S.
Munier, Mathilde
Ngov, Chheng
Tritsch, Denis
Lièvremont, Didier
Rohmer, Michel
Grosdemange-Billiard, Catherine
author_facet Dreneau, Aurore
Krebs, Fanny S.
Munier, Mathilde
Ngov, Chheng
Tritsch, Denis
Lièvremont, Didier
Rohmer, Michel
Grosdemange-Billiard, Catherine
author_sort Dreneau, Aurore
collection PubMed
description Three α,α-difluorophosphonate derivatives of fosmidomycin were synthesized from diethyl 1,1-difluorobut-3-enylphosphonate and were evaluated on Escherichia coli. Two of them are among the best 1-deoxy-d-xylulose 5-phosphate reductoisomerase inhibitors, with IC(50) in the nM range, much better than fosmidomycin, the reference compound. They also showed an enhanced antimicrobial activity against E. coli on Petri dishes in comparison with the corresponding phosphates and the non-fluorinated phosphonate.
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spelling pubmed-83979562021-08-29 α,α-Difluorophosphonohydroxamic Acid Derivatives among the Best Antibacterial Fosmidomycin Analogues Dreneau, Aurore Krebs, Fanny S. Munier, Mathilde Ngov, Chheng Tritsch, Denis Lièvremont, Didier Rohmer, Michel Grosdemange-Billiard, Catherine Molecules Article Three α,α-difluorophosphonate derivatives of fosmidomycin were synthesized from diethyl 1,1-difluorobut-3-enylphosphonate and were evaluated on Escherichia coli. Two of them are among the best 1-deoxy-d-xylulose 5-phosphate reductoisomerase inhibitors, with IC(50) in the nM range, much better than fosmidomycin, the reference compound. They also showed an enhanced antimicrobial activity against E. coli on Petri dishes in comparison with the corresponding phosphates and the non-fluorinated phosphonate. MDPI 2021-08-23 /pmc/articles/PMC8397956/ /pubmed/34443699 http://dx.doi.org/10.3390/molecules26165111 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Dreneau, Aurore
Krebs, Fanny S.
Munier, Mathilde
Ngov, Chheng
Tritsch, Denis
Lièvremont, Didier
Rohmer, Michel
Grosdemange-Billiard, Catherine
α,α-Difluorophosphonohydroxamic Acid Derivatives among the Best Antibacterial Fosmidomycin Analogues
title α,α-Difluorophosphonohydroxamic Acid Derivatives among the Best Antibacterial Fosmidomycin Analogues
title_full α,α-Difluorophosphonohydroxamic Acid Derivatives among the Best Antibacterial Fosmidomycin Analogues
title_fullStr α,α-Difluorophosphonohydroxamic Acid Derivatives among the Best Antibacterial Fosmidomycin Analogues
title_full_unstemmed α,α-Difluorophosphonohydroxamic Acid Derivatives among the Best Antibacterial Fosmidomycin Analogues
title_short α,α-Difluorophosphonohydroxamic Acid Derivatives among the Best Antibacterial Fosmidomycin Analogues
title_sort α,α-difluorophosphonohydroxamic acid derivatives among the best antibacterial fosmidomycin analogues
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8397956/
https://www.ncbi.nlm.nih.gov/pubmed/34443699
http://dx.doi.org/10.3390/molecules26165111
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