2020
DOI: 10.3390/molecules25245940
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(Z,Z)-Selanediylbis(2-propenamides): Novel Class of Organoselenium Compounds with High Glutathione Peroxidase-Like Activity. Regio- and Stereoselective Reaction of Sodium Selenide with 3-Trimethylsilyl-2-propynamides

Abstract: The efficient regio- and stereoselective synthesis of (Z,Z)-3,3′-selanediylbis(2-propenamides) in 76–93% yields was developed based on the reaction of sodium selenide with 3-trimethylsilyl-2-propynamides. (Z,Z)-3,3′-Selanediylbis(2-propenamides) are a novel class of organoselenium compounds. To date, not a single representative of 3,3′-selanediylbis(2-propenamides) has been described in the literature. Studying glutathione peroxidase-like properties by a model reaction showed that the activity of the obtained … Show more

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Cited by 7 publications
(10 citation statements)
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“…The synthesis of various vinylic selenides is within the scope of our scientific interests, and a number of effective methods for the preparation of functionalized vinyl and divinyl selenides, including unsubstituted divinyl selenide, have been previously developed [39][40][41][42][43][44][45][46].…”
Section: Resultsmentioning
confidence: 99%
“…The synthesis of various vinylic selenides is within the scope of our scientific interests, and a number of effective methods for the preparation of functionalized vinyl and divinyl selenides, including unsubstituted divinyl selenide, have been previously developed [39][40][41][42][43][44][45][46].…”
Section: Resultsmentioning
confidence: 99%
“…9 Organoselenium compounds exhibit glutathione peroxidase-like properties and can be used to treat diseases associated with oxidative stress, such as ischemic stroke, cardiovascular, Alzheimer's and Parkinson's disease. 10–13…”
Section: Introductionmentioning
confidence: 99%
“…9 Organoselenium compounds exhibit glutathione peroxidase-like properties and can be used to treat diseases associated with oxidative stress, such as ischemic stroke, cardiovascular, Alzheimer's and Parkinson's disease. [10][11][12][13] Ebselen is the best-known organoselenium synthetic drug that mimics the catalytic activity of glutathione peroxidase. [14][15][16][17] Ebselen acts as a catalyst in converting hydrogen peroxide to harmless water molecules.…”
Section: Introductionmentioning
confidence: 99%
“…Recently we developed the efficient regio- and stereoselective synthesis of the novel class of divinyl selenides, ( Z,Z )-3,3′-selanediylbis(2-propenamides), based on the reaction of sodium selenide with 3-trimethylsilyl-2-propynamides [ 64 ]. Like ebselen, these products contain the amide function.…”
Section: Introductionmentioning
confidence: 99%
“…Like ebselen, these products contain the amide function. The compounds with high glutathione peroxidase-like activity were found among ( Z,Z )-3,3′-selanediylbis(2-propenamides) [ 64 ].…”
Section: Introductionmentioning
confidence: 99%