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

Eric Lattmann; Simon Dunn; Suwanna Niamsanit; Nison Sattayasai

doi:10.1016/j.bmcl.2004.12.051

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

Khon Kaen University

Research output: Contribution to journal › Article › peer-review

83 Citations (Scopus)

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 language	English
Pages (from-to)	919-921
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	15
Issue number	4
DOIs	https://doi.org/10.1016/j.bmcl.2004.12.051
Publication status	Published - 15 Feb 2005

Keywords

2(5H)-Furanones
Antibacterials
Bioactivity
Synthesis

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10.1016/j.bmcl.2004.12.051

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title = "Synthesis and antibacterial activities of 5-hydroxy-4-amino-2(5H)-furanones",

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. {\textcopyright} 2005 Elsevier Ltd. All rights reserved.",

keywords = "2(5H)-Furanones, Antibacterials, Bioactivity, Synthesis",

author = "Eric Lattmann and Simon Dunn and Suwanna Niamsanit and Nison Sattayasai",

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T1 - Synthesis and antibacterial activities of 5-hydroxy-4-amino-2(5H)-furanones

AU - Lattmann, Eric

AU - Dunn, Simon

AU - Niamsanit, Suwanna

AU - Sattayasai, Nison

PY - 2005/2/15

Y1 - 2005/2/15

N2 - 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.

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.

KW - 2(5H)-Furanones

KW - Antibacterials

KW - Bioactivity

KW - Synthesis

UR - https://www.scopus.com/pages/publications/16244368469

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U2 - 10.1016/j.bmcl.2004.12.051

DO - 10.1016/j.bmcl.2004.12.051

M3 - Article

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SN - 0960-894X

VL - 15

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EP - 921

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

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ER -

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

Abstract

Keywords

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