Synthesis and antibacterial activities of 5-hydroxy-4-amino-2(5H)-furanones

Eric Lattmann*, Simon Dunn, Suwanna Niamsanit, Nison Sattayasai

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

Starting from the mucohalogen acids 1a and b 5-hydroxy-2(5H)-furanones 2a-h have been prepared and tested. These novel 4-amino-5-hydroxy 2(5H)-furananones have shown a broad antibiotic activity against Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853 in the micromolar range. A one step synthesis from mucohalogen acids towards the antibacterials 2a-h was developed, in which the target was obtained from 1a and b under reflux in toluene in presence of a catalytic amount of sulfuric acid. The derivatives 2b and c displayed a MIC and MBC of 4/8 μg/ml, against Staphylococcus aureus with a selectivity towards the resistant strains. © 2005 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)919-921
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume15
Issue number4
DOIs
Publication statusPublished - 15 Feb 2005

Fingerprint

Staphylococcus aureus
Acids
Toluene
Pseudomonas aeruginosa
Escherichia coli
Anti-Bacterial Agents
Derivatives
butenolide
sulfuric acid

Keywords

  • 2(5H)-Furanones
  • Antibacterials
  • Bioactivity
  • Synthesis

Cite this

Lattmann, Eric ; Dunn, Simon ; Niamsanit, Suwanna ; Sattayasai, Nison. / Synthesis and antibacterial activities of 5-hydroxy-4-amino-2(5H)-furanones. In: Bioorganic and Medicinal Chemistry Letters. 2005 ; Vol. 15, No. 4. pp. 919-921.
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Synthesis and antibacterial activities of 5-hydroxy-4-amino-2(5H)-furanones. / Lattmann, Eric; Dunn, Simon; Niamsanit, Suwanna; Sattayasai, Nison.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 15, No. 4, 15.02.2005, p. 919-921.

Research output: Contribution to journalArticle

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AB - Starting from the mucohalogen acids 1a and b 5-hydroxy-2(5H)-furanones 2a-h have been prepared and tested. These novel 4-amino-5-hydroxy 2(5H)-furananones have shown a broad antibiotic activity against Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853 in the micromolar range. A one step synthesis from mucohalogen acids towards the antibacterials 2a-h was developed, in which the target was obtained from 1a and b under reflux in toluene in presence of a catalytic amount of sulfuric acid. The derivatives 2b and c displayed a MIC and MBC of 4/8 μg/ml, against Staphylococcus aureus with a selectivity towards the resistant strains. © 2005 Elsevier Ltd. All rights reserved.

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