Preparation of bis(2-pyridyl) diselenide derivatives: Synthesis of selenazolo[5,4-b]pyridines and unsymmetrical diorganyl selenides, and evaluation of antioxidant and anticholinesterasic activities

Peglow, Thiago J.; Schumacher, Ricardo F.; Cargnelutti, Roberta; Reis, Angélica S.; Luchese, Cristiane; Wilhelm, Ethel A.; Perin, Gelson

doi:10.1016/j.tetlet.2017.08.030

Cited by 53 publications

(51 citation statements)

References 39 publications

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“…In terms of selenide effects on memory, we are only aware of a few published reports to date (Bortolatto et al 2013b ; Duarte et al 2017 ; Peglow et al 2017 ; Ramalho et al 2018 ; Yan et al 2019 ).…”

Section: Pharmacology Of Organoselenium Compoundsmentioning

confidence: 99%

“…The pioneering article of Muller and collaborators, demonstrating the GPx-like activity of ebselen (Mϋller et al 1984 ), opened new avenues in the field of organoselenium applications and, since that, a multitude of synthetic entities with different chemical characteristics has been synthesized and their antioxidant properties investigated. As a result, major databases have been flooded with research articles related to antioxidant, GPx-like, radical-, and peroxynitrite-scavenging activities of newly developed molecules (Bortolatto et al 2013a ; Chagas et al 2015 ; Fonseca et al 2015 ; Ibrahim et al 2012a , b , 2014a , 2019 ; Junior et al 2017 ; Luchese et al 2012a ; Peglow et al 2017 ; Phadnis et al 2014 ; Sauer et al 2017 ; Singh et al 2019 ; Stefanello et al 2015a ; Talas et al 2015 ).…”

Section: Pharmacology Of Organoselenium Compoundsmentioning

confidence: 99%

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Toxicology and pharmacology of synthetic organoselenium compounds: an update

2021

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Here, we addressed the pharmacology and toxicology of synthetic organoselenium compounds and some naturally occurring organoselenium amino acids. The use of selenium as a tool in organic synthesis and as a pharmacological agent goes back to the middle of the nineteenth and the beginning of the twentieth centuries. The rediscovery of ebselen and its investigation in clinical trials have motivated the search for new organoselenium molecules with pharmacological properties. Although ebselen and diselenides have some overlapping pharmacological properties, their molecular targets are not identical. However, they have similar anti-inflammatory and antioxidant activities, possibly, via activation of transcription factors, regulating the expression of antioxidant genes. In short, our knowledge about the pharmacological properties of simple organoselenium compounds is still elusive. However, contrary to our early expectations that they could imitate selenoproteins, organoselenium compounds seem to have non-specific modulatory activation of antioxidant pathways and specific inhibitory effects in some thiol-containing proteins. The thiol-oxidizing properties of organoselenium compounds are considered the molecular basis of their chronic toxicity; however, the acute use of organoselenium compounds as inhibitors of specific thiol-containing enzymes can be of therapeutic significance. In summary, the outcomes of the clinical trials of ebselen as a mimetic of lithium or as an inhibitor of SARS-CoV-2 proteases will be important to the field of organoselenium synthesis. The development of computational techniques that could predict rational modifications in the structure of organoselenium compounds to increase their specificity is required to construct a library of thiol-modifying agents with selectivity toward specific target proteins.

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Section: Pharmacology Of Organoselenium Compoundsmentioning

confidence: 99%

Section: Pharmacology Of Organoselenium Compoundsmentioning

confidence: 99%

Toxicology and pharmacology of synthetic organoselenium compounds: an update

2021

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“…Recently, we reported the preparation of bis(2-pyridyl) diselenide derivatives and their antioxidant and anticholinesterasic activities. 35 Based on our previous findings and in those from Zang and coworkers, 36 we hypothesize that these compounds could be ideal starting materials to synthesize fused selenopheno [2,3-b]pyridines by the reaction with terminal alkynes in the presence of a nitrosating agent (Scheme 2). Scheme 2.…”

Section: Introductionmentioning

confidence: 91%

Synthesis of 2-organylselenopheno[2,3-b]pyridines and 1,6-diazaselenanthrenes via radical cascade reactions using tert-butyl nitrite

Perin¹,

Peglow²,

Bartz³

et al. 2019

Arkivoc

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We describe herein an alternative method to prepare 2-organylselenopheno [2,3-b]pyridines starting from bis(3-amino-2-pyridyl) diselenide and aryl-and alkylacetylenes in the presence of t BuONO in CH3NO2 as solvent. The reactions were conducted at 80 °C for 2 hours, and six selenopheno[2,3-b]pyridine derivatives were obtained in satisfactory yields, ranging from 10% to 41%. Using the same conditions, but in the absence of the alkyne counterpart, three new 1,6-diazaselenanthrenes were obtained with yields ranging from 41% to 47%. These compounds are unknown in the literature.

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“…[15][16][17][18][19][20] They have been termed as Janus element owing to their both nucleophilic and electrophilic characteristics. [20][21][22][23][24][25] Thereby, organoselenium compounds have become quite an attraction amongst the researchers when it comes to organic chemistry, [26,27] alongside their impact in the field of medicinal chemistry, [28,29] material chemistry, [30] chemical biology [31,32] and biochemistry. [33]…”

Section: Introductionmentioning

confidence: 99%

Insights into the Recent Synthetic Advances of Organoselenium Compounds

2021

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The ever-growing interest for organoselenium compounds amongst the chemists has made commendable impact in the field of medicinal chemistry, material chemistry, chemical biology and biochemistry. Researchers have progressively contributed in the development of organoselenium compounds over the years which has been periodically reviewed. On the similar note, this review attempts at providing an overview of the recent advances made in organoselenium chemistry while covering their catalytic indulgence in different transformational approaches, their role in asymmetric synthesis, and synthetic approaches steering their synthesis. These approaches encompass selenofunctionalization and/or cyclization, electrochemical selenylation, bromolactonization, [2,3]-or [1,2]-sigmatropic rearrangement reactions among others. Herein, we have focused on the synthetic approaches developed for the past three years that have not been covered in previously reviewed scientific material. With the knowledge of the recent progress covered, this review could contribute towards future development of organoselenium compounds along with the improvement of the current status.

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Preparation of bis(2-pyridyl) diselenide derivatives: Synthesis of selenazolo[5,4-b]pyridines and unsymmetrical diorganyl selenides, and evaluation of antioxidant and anticholinesterasic activities

Cited by 53 publications

References 39 publications

Toxicology and pharmacology of synthetic organoselenium compounds: an update

Toxicology and pharmacology of synthetic organoselenium compounds: an update

Synthesis of 2-organylselenopheno[2,3-b]pyridines and 1,6-diazaselenanthrenes via radical cascade reactions using tert-butyl nitrite

Insights into the Recent Synthetic Advances of Organoselenium Compounds

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