(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
“…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].…”
First examples of the reactions of 3-trimethylsilyl-2-propynamides with organic diselenides yielding 3-alkylselanyl-2-propenamides and 3-organylselanyl-2-propynamides were realized. The latter compounds were obtained by the Cu-catalyzed reaction of organic diselenides with 4-propioloylmorpholine. The reaction of 3-trimethylsilyl-2-propynamides with dialkyl diselenides in the system NaBH4/H2O/K2CO3/THF proceeded in a regio- and stereoselective fashion, affording 3-alkylselanyl-2-propenamides in 90–94% yields. An unsymmetrical divinyl selenide with the cyclic amide groups and a product, containing two selanyl-2-propenamide moieties and three cyclic amide groups, were synthesized. The Cu-catalyzed allylation reaction of 3-trimethylsilyl-2-propynamides was accompanied with desilylation to yield 3-allyl-2-propynamides.
“…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].…”
First examples of the reactions of 3-trimethylsilyl-2-propynamides with organic diselenides yielding 3-alkylselanyl-2-propenamides and 3-organylselanyl-2-propynamides were realized. The latter compounds were obtained by the Cu-catalyzed reaction of organic diselenides with 4-propioloylmorpholine. The reaction of 3-trimethylsilyl-2-propynamides with dialkyl diselenides in the system NaBH4/H2O/K2CO3/THF proceeded in a regio- and stereoselective fashion, affording 3-alkylselanyl-2-propenamides in 90–94% yields. An unsymmetrical divinyl selenide with the cyclic amide groups and a product, containing two selanyl-2-propenamide moieties and three cyclic amide groups, were synthesized. The Cu-catalyzed allylation reaction of 3-trimethylsilyl-2-propynamides was accompanied with desilylation to yield 3-allyl-2-propynamides.
“…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.…”
The synthetic application of the new reagent, 1,2-bis[(Z)-2-(vinylsulfanyl)ethenyl] diselane, was described for the first time. This reagent was obtained in high yield by a chemo-, regio- and stereoselective reaction of...
“…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 ].…”
Highly efficient stereoselective syntheses of novel bis(E-2-chlorovinyl) selenides and bis(E-2-bromovinyl) selenides in quantitative yields by reactions of selenium dichloride and dibromide with alkynes were developed. The reactions proceeded at room temperature as anti-addition giving products exclusively with (E)-stereochemistry. The glutathione peroxidase-like activity of the obtained products was estimated and compounds with high activity were found. The influence of substituents in the products on their glutathione peroxidase-like activity was discussed.
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