(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 products significantly varies depending on the organic moieties in the amide group. Divinyl selenide, which contains two lipophilic cyclohexyl substituents in the amide group, exhibits very high glutathione peroxidase-like activity and this compound is considerably superior to other products in this respect.

First Examples of Reactions of 3-Trimethylsilyl-2-Propynamides and Organic Diselenides: Synthesis of Novel Derivatives of 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].…”

Polyunsaturated sulfur/selenium-containing products based on regio- and stereoselective nucleophilic addition and substitution reactions of 1,2-bis[(Z)-2-(vinylsulfanyl)ethenyl] diselane

“…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…”

“…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.…”

Selenium Dihalides Click Chemistry: Highly Efficient Stereoselective Addition to Alkynes and Evaluation of Glutathione Peroxidase-Like Activity of Bis(E-2-halovinyl) Selenides

“…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.…”

“…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 ].…”