Estratégias para a síntese de γ-alquilidenobutenolídeos

Barbosa, Luiz C. A.; Teixeira, Róbson Ricardo; Pinheiro, Patrícia Fontes; Maltha, Célia R. A.; Demuner, Antônio J.

doi:10.1590/s0100-40422010000500030

Cited by 6 publications

(5 citation statements)

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“…Previous studies have drawn attention to the class of compounds of butenolides, which represent a large family of γ-lactones that have a common subunit known as furan-2(5 H )-one (Figure ). These lactones are found in many natural sources and are associated with a wide variety of biological activities, including antibiotics, anti-inflammatory agents, phytotoxicity, and insecticide. , Some halogenated furanones known as fimbrolides, produced by the red seaweed Delisea pulchra, have been reported as natural biofilm-inhibiting compounds. These compounds (Figure ) have been shown to inhibit the biofilm formation of Escherichia coli, Bacillus subtilis, and Pseudomonas aeruginosa. − The synthesis of other similar lactones (type A and type B, Figure ) and the evaluation against the formation of Salmonella typhimurium biofilm revealed that the major impact is caused by the bromination pattern, since the A type compounds that have the bromine atom in position 4 are more active than type B …”

Section: Introductionmentioning

confidence: 99%

“…15 Previous studies have drawn attention to the class of compounds of butenolides, which represent a large family of γ-lactones that have a common subunit known as furan-2(5H)-one (Figure 1). 16 These lactones are found in many natural sources and are associated with a wide variety of biological activities, including antibiotics, anti-inflammatory agents, phytotoxicity, and insecticide. 16,17 Some halogenated furanones known as fimbrolides, produced by the red seaweed Delisea pulchra, have been reported as natural biofilm-inhibiting compounds.…”

Section: ■ Introductionmentioning

confidence: 99%

“…16 These lactones are found in many natural sources and are associated with a wide variety of biological activities, including antibiotics, anti-inflammatory agents, phytotoxicity, and insecticide. 16,17 Some halogenated furanones known as fimbrolides, produced by the red seaweed Delisea pulchra, have been reported as natural biofilm-inhibiting compounds. These compounds (Figure 1) have been shown to inhibit the biofilm formation of Escherichia coli, Bacillus subtilis, and Pseudomonas aeruginosa.…”

Section: ■ Introductionmentioning

confidence: 99%

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Syntheses of Six Tetronamides and Evaluation as Biofilm Inhibitors against the Citrus Canker Bacterial-Pathogen Xanthomonas citri ssp. citri

Cardoso,

Li,

Pereira

et al. 2023

ACS Agric. Sci. Technol.

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Small molecules from the family of γ-lactones have a wide variety of biological activities, including antibiotics and biofilm inhibitors against bacterial pathogens. In the present study, a group of six β-arylamino-γ-lactones known as tetronamides were synthesized from reduced mucobromic acid and different anilines (38–77%). The compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectrometry (MS). The six tetronamides were evaluated for antimicrobial and antibiofilm activity against the plant bacterial pathogen Xanthomonas citri ssp. citri (Xcc), which causes citrus canker, one of the most devastating citrus diseases worldwide. Four compounds (3b, 3d, 3e, and 3f) showed a minimum inhibitory concentration (MIC) against Xcc of 500 μg/mL, while the other two (3a and 3c) had a MIC against Xcc of 1000 μg/mL. The bacterial biofilm inhibition activity was evaluated by testing the concentrations between 0 and 125 μg/mL. The results showed that all the six compounds inhibited the biofilm formation at concentrations lower than MIC. The best performances in biofilm inhibition were recorded for the compounds with the presence of a halogen on the aromatic ring (3b, 3e, and 3f), displaying a median biofilm inhibition concentration (IC50) of 15.4 μg/mL. This study suggested that tetronamides have potential as Xcc biofilm inhibitor to control citrus canker alone or together with other antimicrobials.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Syntheses of Six Tetronamides and Evaluation as Biofilm Inhibitors against the Citrus Canker Bacterial-Pathogen Xanthomonas citri ssp. citri

Cardoso,

Li,

Pereira

et al. 2023

ACS Agric. Sci. Technol.

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“…symbiont partner within lichen Peltigera canina. These compounds possess a g-benzylidene functionality and belong to the class of substances known as g-alkylidenebutenolides [17,18]. These nostoclides displayed moderate cytotoxic effects against the mouse neuroblastoma cell lines Neuro-2aCCL and KB CCL 17 [19].…”

Section: Introductionmentioning

confidence: 99%

Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues

Teixeira

Barbosa

Antolínez

et al. 2016

Journal of Molecular Structure

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We have here elucidated the crystal structures of five nostoclide analogues. A common feature in all compounds is a substituent at the para-position of the benzylidene group. Compounds with either bromine (3) or hydroxyl (4) as para-substituent crystallizes with Z' ¼ 2 as result of conformerism. It was also observed that Z' > 1 in the compound with a para-dimethylamino substituent (1). However, its four crystallographically independent molecules are conformationally similar. They are not related by crystallographic symmetry due to the offset packing of their CeH … O]C nonclassical hydrogen bonded double chains. This compound (1) has also crystallized in a chiral space group (P2 1 ) despite the lack of a stereocenter. Such enantiomorphism phenomenon is related to the presence of only one of the two mirror benzyl conformations with phenyl ring at the equatorial position opposite the lactone oxygen atom. The molecular mean plane of nostoclide analogues has been featured by high level of planarity, except in the brominated compound where two twisted conformations occurred due to rotations on the single bond axis into benzylidene group. The benzyl conformation has been the greatest difference between the two crystallographically independent molecules of the para-hydroxylated compound (4). The crystal packing of the compounds is marked by double catemer motif assembled through CeH … O] C non-classical hydrogen bonds, although CeH … p interactions do play an important role in stabilizing the crystal packing of some compounds of the series.

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“…O butenolídeo 9 1 é um excelente material de partida para sín-teses orgânicas pois, além de ser densamente funcionalizado, está disponível comercialmente ou é preparado em uma etapa e em alto rendimento, através da bromação do furfural (3, oriundo de biomassa) empregando-se água como solvente (Esquema 1). 10 Por sua vez, a furanona 2 é facilmente obtida a partir da redução de 1 com NaBH 4 , em escala multigrama (Esquema 2).…”

Section: Introductionunclassified

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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Estratégias para a síntese de γ-alquilidenobutenolídeos

Cited by 6 publications

References 56 publications

Syntheses of Six Tetronamides and Evaluation as Biofilm Inhibitors against the Citrus Canker Bacterial-Pathogen Xanthomonas citri ssp. citri

Syntheses of Six Tetronamides and Evaluation as Biofilm Inhibitors against the Citrus Canker Bacterial-Pathogen Xanthomonas citri ssp. citri

Conformerism, enantiomorphism and double catemer motifs in para-substituted nostoclide analogues

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

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