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

Lattmann, Eric; Dunn, S. Patrick; Niamsanit, Suwanna; Sattayasai, Nison

doi:10.1016/j.bmcl.2004.12.051

Cited by 67 publications

(40 citation statements)

References 13 publications

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“…Furanone-containing materials are reported to have a broad range of biological and physiological properties including antitumor, antibiotic, haemorrhagic and insecticidal activity [23][24][25][26]. The biological mechanism of these derivatives is still under investigation [24].…”

Section: Resultsmentioning

confidence: 99%

“…The biological mechanism of these derivatives is still under investigation [24]. To explore the application of these compounds in dental research, we synthesized a photocurable furanone derivative and applied it to dental resin composites.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, it has been reported that human saliva can significantly reduce the antibacterial activity of the QAS-containing restoratives, probably due to electrostatic interactions between QAS and proteins in saliva [21][22]. Recently furanone derivatives have been found to have strong antitumor [23] and antibacterial functions [24]. In the study, we would like to explore them in dental applications.…”

Section: Introductionmentioning

confidence: 99%

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A Novel Antibacterial Dental Resin Composite

Weng¹,

Chong²,

Howard³

et al. 2012

JBNB

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This study reports the synthesis and evaluation of a novel furanone-containing antibacterial resin composite. Compressive strength (CS) and S. mutans viability were used to evaluate the mechanical strength and antibacterial activity of the composites. With 5% to 30% addition of the furanone derivative, the composite showed no change in CS but a significant antibacterial activity with a 16% -68% reduction in the S. mutans viability. Further, the antibacterial activity of the modified composite was not affected by human saliva. The aging study implies that the modified composite may have a long-lasting antibacterial function. Within the limitations of this study, it appears that this experimental resin composite may potentially be developed into a clinically attractive dental restorative due to its high mechanical strength and antibacterial function.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A Novel Antibacterial Dental Resin Composite

Weng¹,

Chong²,

Howard³

et al. 2012

JBNB

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“…22 A piridazinona 23 foi sintetizada em meio aquoso a partir da reação da hidrazina (24) α-bromo-enaminonas 28a-c, cujos rendimentos não foram descritos (Esquema 13). 23 Apesar do histórico de enaminonas com atividade antibacteriana, as moléculas 28a-c não apresentaram bioatividade significativa. 24 Ainda buscando potenciais antimicrobianos, Lattmann reportou a síntese de 3-bromo-4-imidazo-5-metóxi-2-furanonas (29a-d).…”

Section: Reação Do áCido Mucobrômico Com Heteronucleófilosunclassified

Aplicações sintéticas do ácido mucobrômico e da 3,4-dibromofuran-2(5H)-ona

Cunha¹,

Oliveira²

2011

Quím. Nova

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Recebido em 23/11/10; aceito em 1/4/11; publicado na web em 10/6/11 SYNTHETIC APPLICATIONS OF MUCOBROMIC ACID AND 3,4-DIBROMOFURAN-2(5H)-ONE. This review describes the use of two biomass-derivate butenolides as intermediates in organic synthesis, mucobromic acid and its reduced derivative 3,4-dibromofuran-2(5H)-one. The ambiphilic and ambident character of such butenolides make them versatile starting materials in the synthesis of natural and/or bioactive compounds. Thus, the reactions of mucobromic acid with C-nucleophiles and heteronucleophiles are described, as well as the nucleophilic addition to carbonyl reactions of 3,4-dibromofuran-2(5H)-one. Besides, both compounds are active in diverse metal cross-coupling reactions, manly with palladium in Suzuki and Sonogashira reactions.Keywords: mucobromic acid; 3,4-dibromofuran-2(5H)-one; butenolides. INTRODUÇÃOA ciência Síntese Orgânica passa por um momento de revitalização que inclui, entre outros aspectos, a preocupação com a eficiência da metodologia sintética e sua aplicação numa síntese total, quer seja um produto natural ou uma substância valorada por suas propriedades biológicas ou físico-químicas.1-3 A incorporação de materiais de partida obtidos de fontes renováveis, a preocupação com o menor consumo de energia, o emprego de métodos e técnicas para acelerar e/ou promover reações antigas e novas passaram a ser metas do planejamento sintético.4,5 Estas modificações podem ser relacionadas com incrementos no design experimental. Desta forma, Carlson propôs o conceito da reação ideal, que deve ser realizada em água, o material de partida de fácil acesso, barato, não tóxico e o produto facilmente isolado em rendimento quantitativo. 6 Complementarmente, Wender preconizou que a economia de etapas é o fator de maior influência na viabilidade de uma síntese, pois determina tempo, custo, geração de resíduos e escala do processo.7 Portanto, novas reações devem ser desenvolvidas para que os princípios da Química Verde sejam atendidos.8 Estas condições de idealidade para uma síntese norteiam os desafios a serem perseguidos pela comunidade sintética no século atual.Uma das formas de se obter, em poucas etapas, um aumento significativo de complexidade estrutural consiste em empregar molé-culas polifuncionalizadas ambifílicas e polidentadas de fácil acesso, que possam, assim, atuar como eletrófilos e/ou nucleófilos. Dentre as que apresentam todas estas características, merecem destaque as furanonas halogenadas como o ácido mucobrômico (1) e o seu derivado reduzido, a 3,4-dibromofuran-2(5H)-ona (2) (Figura 1).

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“…However, it has been reported that human saliva can significantly decrease the antibacterial activity of the QAScontaining restoratives, probably due to electrostatic interactions between QAS and proteins in saliva [25,26]. Recently furanone derivatives have been found to have strong antitumor [27,28] and antibacterial functions [29]. These compounds all contain a furanone structure (classified as lactone or butenolide) and showed a similarity to natural manoalide, which has an interesting anti-inflammatory activity [30].…”

Section: Introductionmentioning

confidence: 99%

Preparation and evaluation of a novel antibacterial glass-ionomer cement

Howard¹,

Weng²,

Huang³

et al. 2013

JBiSE

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A novel antibacterial glass-ionomer cement has been developed. Compressive strength (CS) and S. mutans viability were used to evaluate the mechanical strength and antibacterial activity of the formed cement. Compressive yield strength (YS), modulus (M), diametral tensile strength (DTS) and flexural strength (FS) were also determined. All the formulated antibacterial cements showed a significant antibacterial activity, accompanying with an initial CS reduction. The effect of the synthesized antibacterial polymer loading was significant. Increasing loading from 1% to 20% significantly decreased the S. mutans viability from 3% to 50% and also reduced the initial CS (325 MPa) of the formed cements from 19% to 75%. The cement with 5% antibacterial polymer loading showed 142 MPa, 6.9 GPa, 224 MPa, 52 MPa, and 62 MPa in YS, M, CS, DTS and FS, respectively, as compared to 170, 7.1, 325, 60 and 87 for the experimental cement without antibacterial polymer addition and 141, 6.9, 236, 42 and 53 for Fuji II LC. It was also found that the chlorine-containing antibacterial cement showed better CS values than the bromine-containing cement, with no significant difference in antibacterial activity. The antibacterial cement also showed a similar antibacterial activity to Streptococcus mutans, lactobacillus, Staphylococcus aureus and Staphylococcus epidermidis. The human saliva did not affect the antibacterial activity of the cement. The thirty-day aging study indicates that the cements may have a longlasting antibacterial function.

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

Cited by 67 publications

References 13 publications

A Novel Antibacterial Dental Resin Composite

A Novel Antibacterial Dental Resin Composite

Aplicações sintéticas do ácido mucobrômico e da 3,4-dibromofuran-2(5H)-ona

Preparation and evaluation of a novel antibacterial glass-ionomer cement

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