Electrochemical Selenation/Cyclization of Quinones: A Rapid, Green and Efficient Access to Functionalized Trypanocidal and Antitumor Compounds

Kharma, Ammar; Jacob, Claus; Bozzi, Ícaro A. O.; Jardim, Guilherme A. M.; Braga, Antônio L.; Salomão, Kelly; Gatto, Claudia C.; Silva, Maria Francilene S.; Pessoa, Cláudia; Stangier, Maximilian; Ackermann, Lutz; Júnior, Eufrânio N. da Silva

doi:10.1002/ejoc.202000216

Cited by 55 publications

(49 citation statements)

References 82 publications

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“…The developed green synthetic method provided 40 examples, with yields ranging from 54% to 88%. The electrochemical selenylation/cyclization of naphthoquinones was described by Da Silva Júnior and co-workers [48] as an efficient and reliable method for the achievement of molecules with great biological potential: 44 and 45 (Scheme 20). A wide range of selenium-containing multifunctional redox quinoidal compounds has been synthesized by using lapachol 43 or lawsone derivatives-in undivided electrochemical cells-diselenides 6 (1.0 equivalent), nBu4NPF6 (1.0 equivalent) as electrolyte and acetonitrile as solvent.…”

Section: Electrochemically Promoted Reactionsmentioning

confidence: 99%

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

et al. 2022

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Organoselenium compounds have been successfully applied in biological, medicinal and material sciences, as well as a powerful tool for modern organic synthesis, attracting the attention of the scientific community. This great success is mainly due to the breaking of paradigm demonstrated by innumerous works, that the selenium compounds were toxic and would have a potential impact on the environment. In this update review, we highlight the relevance of these compounds in several fields of research as well as the possibility to synthesize them through more environmentally sustainable methodologies, involving catalytic processes, flow chemistry, electrosynthesis, as well as by the use of alternative energy sources, including mechanochemical, photochemistry, sonochemical and microwave irradiation.

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Section: Electrochemically Promoted Reactionsmentioning

confidence: 99%

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

et al. 2022

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“…In general, we evaluated compounds containing arylamino [59][60][61][62][63][64], alcohol [60] and alkoxy groups [61,62], selenium and sulfur [65][66][67], the basic chalcone framework [68],…”

Section: Assembly Of a Chemical Library For Virtual Screening Against Mpromentioning

confidence: 99%

Structure-based identification of naphthoquinones and derivatives as novel inhibitors of main protease Mpro and papain-like protease PLpro of SARS-CoV-2

Santos¹,

Kronenberger

Almeida

et al. 2022

Preprint

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The worldwide COVID-19 pandemic caused by the coronavirus SARS-CoV-2 urgently demands novel direct antiviral treatments. The main protease (Mpro) and papain-like protease (PLpro) are attractive drug targets among coronaviruses due to their essential role in processing the polyproteins translated from the viral RNA. In the present work, we virtually screened 688 naphthoquinoidal compounds and derivatives against Mpro of SARS-CoV-2. Twenty-four derivatives were selected and evaluated in biochemical assays against Mpro using a novel fluorogenic substrate. In parallel, these compounds were also assayed with SARS-CoV-2 PLpro. Four compounds inhibited Mpro with half-maximal inhibitory concentration (IC50) values between 0.41 μM and 66 μM. In addition, eight compounds inhibited PLpro with IC50 ranging from 1.7 μM to 46 μM. Molecular dynamics simulations suggest stable binding modes for Mpro inhibitors with frequent interactions with residues in the S1 and S2 pockets of the active site. For two PLpro inhibitors, interactions occur in the S3 and S4 pockets. In summary, our structure-based computational and biochemical approach identified novel naphthoquinonal scaffolds that can be further explored as SARS-CoV-2 antivirals.

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“…Very recently, Ackermann and coworkers investigated an electrochemical oxidative cyclization of quinones and diaryl diselenides using a platinum plate anode and cathode under the constant current (10 mA) in an undivided cell (Scheme 37). 41 Using lapachol 117, the quinone-hybrid compounds 118 were afforded with moderate to high yield via 6-endo-trig way. When this selenylation method was applied to the C-allyl lawsone 121, 5-exo-dig cyclization occurred to give the corresponding products 122 in good to moderate yields.…”

Section: Electrochemically Enabled Selenocyclizationmentioning

confidence: 99%

Recent advances in tandem selenocyclization and tellurocyclization with alkenes and alkynes

et al. 2020

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Electrochemical Selenation/Cyclization of Quinones: A Rapid, Green and Efficient Access to Functionalized Trypanocidal and Antitumor Compounds

Cited by 55 publications

References 82 publications

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

Structure-based identification of naphthoquinones and derivatives as novel inhibitors of main protease Mpro and papain-like protease PLpro of SARS-CoV-2

Recent advances in tandem selenocyclization and tellurocyclization with alkenes and alkynes

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