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

Maxim V Musalov; Vladimir A Potapov; Arkady A Maylyan; Alfiya G Khabibulina; Sergey V Zinchenko; Svetlana V Amosova

doi:10.3390/molecules27031050

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

Molecules. 2022 Feb 3;27(3):1050. doi: 10.3390/molecules27031050.

Authors

Maxim V Musalov¹, Vladimir A Potapov¹, Arkady A Maylyan¹, Alfiya G Khabibulina¹, Sergey V Zinchenko¹, Svetlana V Amosova¹

Affiliation

¹ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.

Abstract

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.

Keywords: alkynes; bis(2-bromovinyl) selenides; bis(2-chlorovinyl) selenides; selenium dibromide; selenium dichloride; stereoselective synthesis.

MeSH terms

Alkynes / chemical synthesis
Alkynes / chemistry*
Catalysis
Click Chemistry*
Glutathione Peroxidase / chemistry
Organoselenium Compounds / chemical synthesis
Organoselenium Compounds / chemistry*
Stereoisomerism

Substances

Alkynes
Organoselenium Compounds
Glutathione Peroxidase