Key steps and intermediates in the catalytic mechanism for the reduction of peroxides by the antioxidant ebselen

Sands, Kai N.; Back, Thomas G.

doi:10.1016/j.tet.2018.05.027

Cited by 35 publications

(28 citation statements)

References 138 publications

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“…These studies showed that all solvents tested led to the product 2 a formation; however, dichloromethane was the solvent that gave the highest yield. Thus, we selected dichloromethane, the best solvent, for the next studies ( Table 1, entries [15][16][17][18][19]. We also observed that the reaction did not proceed without iron(III) chloride ( Table 1, entry 20).…”

Section: Resultsmentioning

confidence: 99%

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Iron‐Mediated Cyclization of 1,3‐Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene‐Fused Chromenes

2020

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The synthesis of selenophene‐fused chromene derivatives starting from 1,3‐diynyl propargyl aryl ethers is reported herein. The method is based on carbon‐carbon, carbon‐selenium, selenium‐carbon and carbon‐selenium bonds formation in a one‐pot protocol, using iron(III) chloride and dibutyl diselenide as promoters. The same reaction conditions were applied to propargyl anilines leading to the formation of 1‐(butylselanyl)‐selenophene quinolines. The results showed that the dilution and temperature of substrate addition had a crucial influence in the products obtained. When the substrates were added at room temperature, in the absence of a solvent, a mixture of products was obtained, whereas the slowly addition (15 min) of starting materials, as a dichloromethane solution, at 0 °C led to the product formation in good yields. The mechanistic study indicates that the cooperative action between iron(III) chloride and dibutyl diselenide was essential to promote the cyclization, whereas separately none of them was effective in promoting the cyclization. We proved the synthetic utility of heterocycles obtained in the Suzuki cross coupling reaction, giving the corresponding cross‐coupled products in good yields. In addition, the organoselenium moiety was removed from the structures of products by using n‐butyllithium.

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Section: Resultsmentioning

confidence: 99%

“…Another feature of our methodology is the introduction of an organoselenium group in the heterocycles, which becomes the final product attractive as a substrate for new organic transformations [16] and for biological studies. [17]…”

Section: Introductionmentioning

confidence: 99%

Iron‐Mediated Cyclization of 1,3‐Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene‐Fused Chromenes

2020

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“…(Adaptado da Ref. 23) Entretanto, em algumas doenças a GPx apresenta-se sobrecarregada devido a produção excessiva de peróxidos e, nesse contexto, moléculas miméticas dessa enzima tornam-se de interesse para que haja o reestabelecimento da homeostase redox. 23 Dos compostos orgânicos contendo selênio já relatados com essa atividade, o ebselen destaca-se por ser o mais estudado.…”

Section: Mecanismo Do Ebselen Como Mimético Da Enzima Glutationa Perounclassified

“…Sabe-se que esse é complexo e altamente dependente dos tipos de substratos utilizados (tióis e hidroperóxidos). 23 Todavia, recentemente, foi proposto um provável mecanismo geral para o ebselen que exibe os principais passos para redução de peróxidos mediante ao consumo de glutationa e outros tióis.…”

Section: Mecanismo Do Ebselen Como Mimético Da Enzima Glutationa Perounclassified

“…Nesse mecanismo revisado, proposto a partir de reações isoladas, é descrito que o ebselen pode reagir por três vias catalíticas (Esquema 3). 23 A primeira é a do selenol ou GPx-like (Esquema 3, A), semelhante ao ciclo da GPx. Nesse mecanismo, na primeira etapa ocorre o ataque de um equivalente de tiol ao ebselen 1 levando à formação do sulfeto de selenenila 6.…”

Section: Mecanismo Do Ebselen Como Mimético Da Enzima Glutationa Perounclassified

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Ebselen: A Brief Review of its Antioxidant Capacity and Biological Applications

Nascimento¹,

Cordeiro²,

Silva³

2019

Rev. Virtual Quim.

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Ebselen is a low toxicity selenium heterocycle very studied for its antiinflammatory and antioxidant activity. In this context, ebselen is capable to mimic the glutathione peroxidase (GPx) catalytic activity, which is very important to protect cellular components from damage caused by the accumulation of reactive oxygen species (ROS). Although there are many studies on this compound, there are still divergences on its mechanism of action as GPx mimetic. In this manuscript is present a review of the last 10 years regarding the studies of ebselen mechanisms of action as antioxidant as well as some of its biological application and of its derivatives.

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Oxidation and Reduction

Banerji

2021

Organic Reaction Mechanisms Series

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Key steps and intermediates in the catalytic mechanism for the reduction of peroxides by the antioxidant ebselen

Cited by 35 publications

References 138 publications

Iron‐Mediated Cyclization of 1,3‐Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene‐Fused Chromenes

Iron‐Mediated Cyclization of 1,3‐Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene‐Fused Chromenes

Ebselen: A Brief Review of its Antioxidant Capacity and Biological Applications

Oxidation and Reduction

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