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

Cunha, Sílvio; Oliveira, Caio C.

doi:10.1590/s0100-40422011000800023

Cited by 7 publications

(9 citation statements)

References 31 publications

(38 reference statements)

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“…Compound 6 was obtained in good yield (80%) and on a multigram scale . This compound is a useful template for the preparation of sulfur- and nitrogen-containing heterocycles including agrochemical precursors. , …”

Section: Resultsmentioning

confidence: 93%

“…After evaporation of the solvent under reduced pressure, the crude product was obtained as a solid. This solid was recrystallized in a mixture of hexane/diethyl ether 1:1 (v/v), resulting in the required lactone 2 as white crystals (5.37 g, 22.4 mmol, 80% of yield): mp 89.9−90.5 °C (mp 90−91 °C); 25 IR (KBr) ν ̅ max (cm −1 ) 1758, 1606, 1429, 1339, 1216, 1096, 1023, 992, 981; δ H (CDCl 3 ) 4.87 (2H, s, H-5); δ C (CDCl 3 ) 74.4 (C-5), 114.9 (C-3), 143.8 (C-4), 166.9 (C-2); EI-MS, m/z (%) 244 24), 240 (M •+ , 9), 215 (7), 213 (15), 211 (8), 163 (98), 161 (100), 133 (23), 131 (20), 119 (27), 117 (28), 107 (16), 105 (23), 81 (15), 79 (13), 53 (33).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…The filtrate was concentrated under reduced pressure to yield a dark residue. The purification of this residue by silica gel column chromatography, eluting with a mixture of DCM/hexane of increasing polarity, produced the required compound 7a with 76% yield (1.02 g, 3.8 mmol) and a small amount of 2,2′-dimethoxybiphenyl 8a (1.07 mmol), resulting from the homocoupling of boronic acid: white solid; mp 106.9−107.9 °C; IR (KBr) ν ̅ max (cm 35), 241 (30), 239 (32), 226 (11), 224 (12), 189 (100), 161 (17), 145 (23), 133 (36), 131 (51), 115 (22), 105 (75), 102 (33), 89 (38), 77 (46).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Synthesis of Rubrolide Analogues as New Inhibitors of the Photosynthetic Electron Transport Chain

Barbosa

Maltha

Lage

et al. 2012

J. Agric. Food Chem.

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Many natural products have been used as a model for the development of new drugs and agrochemicals. Following this strategy 11 rubrolide analogues, bearing electron-withdrawing and -donating groups at both benzene rings, were prepared starting from commercially available mucobromic acid. The ability of all compounds to inhibit the photosynthetic electron transport chain in the chloroplast was investigated. The rubrolide analogues were effective in interfering with the light-driven ferricyanide reduction by isolated chloroplasts. The IC(50) values of the most active derivatives are in fact only 1 order of magnitude higher than those of commercial herbicides sharing the same mode of action, such as Diuron (0.27 μM). QSAR studies indicate that the most efficient compounds are those having higher ability to accept electrons, either by a reduction process or by an electrophilic reaction mechanism. The results obtained suggest that the rubrolide analogues represent promising candidates for the development of new active principles targeting photosynthesis to be used as herbicides.

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Section: Resultsmentioning

confidence: 93%

Section: ■ Materials and Methodsmentioning

confidence: 99%

Section: ■ Materials and Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Rubrolide Analogues as New Inhibitors of the Photosynthetic Electron Transport Chain

Barbosa

Maltha

Lage

et al. 2012

J. Agric. Food Chem.

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“…In the last four decades the chemistry of 2(5H)furanones (also referred as 2-butenolides) has received great interest and has experienced a remarkable expansion as evidenced by numeous reviews [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. This interest is largely justified by the fact that these heterocycles include biologically active natural compounds and substances possessing interesting biological properties such as mutagenic, cytotoxic, anti-inflammatory, fungicidal and antibacterial activities.…”

Section: Introductionmentioning

confidence: 99%

“…However, no updated review regarding a comprehensive description of the syntheses of natural and unnatural brominated 2(5H)-furanone derivatives and the biological properties associated to some of these heterocyclic compounds has been published so far. Only two reviews, which were published in 2004 and 2011 respectively, deal with the synthetic aspects of 3,4-dibromo-5-hydroxy-2(5H)-furanone (mucobromic acid) (1) [10,14] and 3,4dibromo-2(5H)-furanone (2) ( Figure 1) [14]. This review with 263 references aims to provide a thorough insight of the synthesis of 2(5H)-furanones with bromine atoms on the heterocyclic ring and/or brominated substituents that include natural products and unnatural compounds used in the literature as versatile synthetic intermediates.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Properties of 2(5H)-Furanones Featuring Bromine Atoms on the Heterocyclic Ring and/or Brominated Substituents

Rossi

Lessi

Manzini

et al. 2017

COC

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This review deals with the synthesis of unnatural and natural 2(5H)-furanone derivatives featuring bromine atoms on the heterocyclic ring and/or brominated substituents, which have been described in the literature since 1951 up to February 2016. The review has been organized on the basis of six classes of brominated furanone derivatives that were synthesized: i) 2(5H)-furanone derivatives with one bromine atom on the heterocyclic ring; ii) 2(5H)-furanone derivatives with two bromine atoms on the heterocyclic ring; iii) 2(5H)-furanone derivatives featuring one bromine atom on the heterocyclic ring and monobrominated substituents; iv) 2(5H)- furanone derivatives featuring one bromine atom on the heterocyclic ring and dibrominated substituents; v) 2(5H)-furanone derivatives with monobrominated substituents; and vi) 2(5H)-furanones featuring dibrominated substituents. Where possible, experimental details of the syntheses have been reported. Furthermore, the biological properties of the target compounds, including their mutagenic, cytotoxic, enzymatic, anti-inflammatory and photosynthetic inhibitory activities have been summarized, paying particular attention on the compounds that have demonstrated antimicrobial properties via inhibition of quorum sensing and biofilm formation

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Late‐Stage Bromination Enables the Synthesis of Rubrolides B, I, K, and O

et al. 2016

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A concise and efficient synthesis of the marine natural products rubrolides B, I, K, and O was accomplished in 3–4 steps from commercially available 3,4‐dichloro‐2(5H)‐furanone. Key steps include: (i) a site‐selective Suzuki cross‐coupling, (ii) a vinylogous aldol condensation, and (iii) a late‐stage bromination. The latter reaction allowed functionalization of the aromatic rings in a highly regioselective fashion, enabling rapid access to the target rubrolides from common precursors.

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

Cited by 7 publications

References 31 publications

Synthesis of Rubrolide Analogues as New Inhibitors of the Photosynthetic Electron Transport Chain

Synthesis of Rubrolide Analogues as New Inhibitors of the Photosynthetic Electron Transport Chain

Synthesis and Biological Properties of 2(5H)-Furanones Featuring Bromine Atoms on the Heterocyclic Ring and/or Brominated Substituents

Late‐Stage Bromination Enables the Synthesis of Rubrolides B, I, K, and O

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