Synthesis of 3-(4-Bromobenzyl)-5-(aryl methylene)-5<i>H</i>-furan-2-ones and Their Activity as Inhibitors of the Photosynthetic Electron  Transport Chain

Barbosa, Luiz C. A.; Rocha, Marcelo Eça; Teixeira, Róbson Ricardo; Maltha, Célia R. A.; Forlani, Giuseppe

doi:10.1021/jf072120x

Cited by 29 publications

(52 citation statements)

References 33 publications

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“…10 The inhibition brought about by the most active brominated analogues was found to be progressively reversed when increasing NH 4 Cl concentrations dissipated the proton gradient across the thylakoid membrane. 9 These results suggest that the synthetic nostoclide analogues may act by inhibiting phosphorylation in chloroplasts, working as energy transfer inhibitors through an interaction with the coupling factor, CF 0 -CF 1 . This mode of action differs from that of commercial herbicides targeting photosynthesis, most of which interact with the electron transport chain, 11 but is similar to that reported for other naturally-occurring phytotoxins.…”

Section: Introductionmentioning

confidence: 88%

“…1: nostoclides; 2: cyanobacterin; 3: 3-benzyl-5-(arylmethylene)furan-2(5H)-ones designed using nostoclides as a lead structure. 9,10 When a group of twelve 3-(4-bromobenzyl)-5-(arylmethylene)furan-2(5H)-ones were synthesized using the nostoclides as a lead structure, several of them were indeed found to inhibit the light-driven reduction of ferricyanide by isolated spinach chloroplasts, the so-called Hill reaction. 9 A second series of 34 non-brominated analogues showed better inhibitory properties, but none of them was capable of completely suppressing the Hill reaction, mostly due to a poor water solubility.…”

Section: Introductionmentioning

confidence: 99%

“…9,10 When a group of twelve 3-(4-bromobenzyl)-5-(arylmethylene)furan-2(5H)-ones were synthesized using the nostoclides as a lead structure, several of them were indeed found to inhibit the light-driven reduction of ferricyanide by isolated spinach chloroplasts, the so-called Hill reaction. 9 A second series of 34 non-brominated analogues showed better inhibitory properties, but none of them was capable of completely suppressing the Hill reaction, mostly due to a poor water solubility. 10 The inhibition brought about by the most active brominated analogues was found to be progressively reversed when increasing NH 4 Cl concentrations dissipated the proton gradient across the thylakoid membrane.…”

Section: Introductionmentioning

confidence: 99%

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Tailoring nostoclide structure to target the chloroplastic electron transport chain

Barbosa¹,

Varejão²,

Petrollino³

et al. 2011

Arkivoc

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Aiming to improve their effectiveness, three modifications were introduced into the structure of the natural phytotoxins nostoclides, leading to the synthesis of novel 3-benzyl-4-isopropyl-5-(arylmethylene)furan-2(5H)-ones, 3-benzyl-5-(furan-2-ylmethylene)furan-2(5H)-ones, and 3,4-dihalo-5-arylidenefuran-2(5H)-ones. All compounds were characterized by IR, 1 H and 13 C NMR, NOEDIF, COSY, HETCOR and MS spectrometry. Increasing the length of the molecule was found to reduce the ability to interfere with ferricyanide reduction by isolated chloroplasts. The addition of an isopropyl moiety into the heterocyclic ring, as in naturally-occurring nostoclides, did not influence the inhibitory potential. Also the replacement of the electron-drawing phenyl substituent with two halogen residues did not improve the resulting activity. However, both latter modifications influenced the interaction with the photosynthetic machinery. These analogues could therefore represent novel leads to be explored toward the development of new herbicides targeting the chloroplastic electron transport chain.

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Section: Introductionmentioning

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Tailoring nostoclide structure to target the chloroplastic electron transport chain

Barbosa¹,

Varejão²,

Petrollino³

et al. 2011

Arkivoc

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“…1). Synthetic efforts led to the preparation of a variety of nostoclide analogs possessing the general structures 3 and 4 [18,19]. It was demonstrated that several analogs were able to significantly inhibit the electron flow in isolated chloroplasts from water to K 3 [Fe(CN) 6 ].…”

Section: Introductionmentioning

confidence: 99%

Phytogrowth Activity of 3-(3-Chlorobenzyl)-5-arylidenefuran-2(5H)-ones

Barbosa¹,

Demuner

Maltha

et al. 2009

Zeitschrift Für Naturforschung B

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Nine new 3-(3-chlorobenzyl)-5-arylidenefuran-2(5H)-ones were prepared in 20 -87 % yields by reaction of 3-(3-chlorobenzyl)furan-2(5H)-one with pertinent aldehydes. All compounds were fully characterized by IR and NMR spectroscopy as well as MS spectrometry. The phytotoxic properties of the synthesized lactones were evaluated as the ability to interfere with the growth of Sorghum bicolor and Cucumis sativus seedlings at 10 ppm and 100 ppm. Lactone 12, at 10 ppm, was the most active and selective, inhibiting the S. bicolor and C. sativus root growth by 70.7 % and 10.7 %, respectively. At 10 ppm, lactone 14 caused the larger effect on the inhibition (41.9 %) of C. sativus. In general, the results indicate the influence of the benzylidene ring substitution on the phytotoxic activity.

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“…Compostos contendo cloro ou bromo no anel do grupo benzila foram também preparados. 61,62 Foi observado que, como uma tendência geral, os compostos não bromados apresentaram atividade inibitória -sobre o transporte de elétrons na reação de Hill -um pouco mais acentuada do que os correspondentes compostos contendo bromo. 57 Foi ainda verificado que vários compostos contendo um átomo de cloro no grupo benzila são capazes de interferir no crescimento radicular das espécies Sorghum bicolor e Cucumis sativus.…”

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Estratégias para a síntese de γ-alquilidenobutenolídeos

Barbosa¹,

Teixeira²,

Pinheiro³

et al. 2010

Quím. Nova

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Recebido em 21/8/09; aceito em 12/1/10; publicado na web em 12/5/10 STRATEGIES FOR THE SYNTHESIS OF g-ALKILIDENEBUTENOLIDES. α,β-unsaturated lactones possessing an alkylidene appendage group at the g-position, are frequently termed g-alkylidenebutenolides. Over the past decades, an increasing number of these compounds have been isolated from various natural sources. Members of this class of substances vary greatly in structural complexity and functionality. Besides that, many of them have been shown to display a wide range of biological activities. The g-alkylidenebutenolides has attracted the attention of the organic synthetic chemists resulting in the development of a variety of process to synthesize them. This article review is concerned with the different approaches that can be utilized to prepare g-alkylidenebutenolides.Keywords: g-alkylidenebutenolides; α,β-unsaturated lactones; butenolides. INTRODUÇÃOButenolídeos correspondem a g-lactonas insaturadas, podendo apresentar anéis dos tipos I ou II (Figura 1).Certos D 3-butenolídeos que possuem um grupo alquilideno localizado na posição g (estrutura geral III, Figura 1) são conhecidos genericamente como g-alquilidenobutenolídeos.Durante as últimas décadas, um grande número de g-alquilidenobutenolídeos foi isolado de várias fontes naturais. Muitos membros dessa família, alguns deles mostrados na Figura 2, apresentam importantes atividades biológicas, incluindo atividade antibiótica, apresentada pelos compostos protoanemonina (1), 1 lissoclinolídeo (8) 6 e rubrolídeos (15-20); 11 inibição da biossíntese do colesterol, observada com as substâncias xerulina (5), ácido xerulínico (6) e diidroxerulina (7); 5 citotoxicidade, observada com os goniobutenolídeos A (10) e B (11) 8 e os nostoclídeos I (12) e II (13). 9 Outros exemplos dessa classe de butenolídeos são os compostos 29-31. A substância 29 é conhecida por ativar a germinação de sementes, 13 enquanto a pirroxantina (30) 14 e peridinina (31) 15 correspondem aos g-alquilidenobutenolídeos de maior complexidade estrutural já isolados e desempenham papel importante na fotossíntese de algas e dinoflagelados, respectivamente.Os g-alquilidenobutenolídeos têm sido considerados atrativos alvos sintéticos devido à diversidade estrutural que apresentam, bem como às suas propriedades biológicas. Como consequência, vários procedimentos sintéticos vêm sendo desenvolvidos para o preparo dessas substâncias. 16 Nesta revisão são descritos vários métodos que podem ser utilizados para a síntese de g-alquilidenobutenolídeos. SÍNTESE DE g-ALQUILIDENOBUTENOLÍDEOS VIA REAÇÕES DE LACTONIZAÇÃO DE g-CETOÁCIDOS, g-HIDROXIÁCIDOS E OUTROS COMPOSTOS CARBONILADOSA reação de lactonização de g-cetoácidos corresponde a um dos primeiros procedimentos desenvolvidos para a síntese de galquilidenobutenolídeos.17 Um exemplo de aplicação desse método é a conversão do ácido g-oxo-pent-2-enoico na substância protoanemonina (1) (Esquema 1).18 Outro exemplo dessa reação é a conversão do ácido 2-hidroxi-2-(4-oxo-tetra-idro-2H-piran-3-il)malônico na desoxi...

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Synthesis of 3-(4-Bromobenzyl)-5-(aryl methylene)-5H-furan-2-ones and Their Activity as Inhibitors of the Photosynthetic Electron Transport Chain

Cited by 29 publications

References 33 publications

Tailoring nostoclide structure to target the chloroplastic electron transport chain

Tailoring nostoclide structure to target the chloroplastic electron transport chain

Phytogrowth Activity of 3-(3-Chlorobenzyl)-5-arylidenefuran-2(5H)-ones

Estratégias para a síntese de γ-alquilidenobutenolídeos

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