Regio- and Stereoselective Synthesis of (Z,Z)-Bis(3-amino-3-oxo-1-propenyl) Selenides and Diselenides Based on 2-propynamides: A Novel Family of Diselenides with High Glutathione Peroxidase-like Activity
The efficient regio- and stereoselective syntheses of (Z,Z)-bis(3-amino-3-oxo-1-propenyl) selenides and diselenides in high yields based on the nucleophilic addition of sodium selenide to 2-propynamides and sodium diselenide to 3-(trimethylsilyl)-2-propynamides have been developed. The first example...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-05-01
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| Series: | Inorganics |
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| Online Access: | https://www.mdpi.com/2304-6740/10/6/74 |
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| author | Vladimir A. Potapov Mikhail V. Andreev Maxim V. Musalov Irina V. Sterkhova Svetlana V. Amosova Lyudmila I. Larina |
| author_facet | Vladimir A. Potapov Mikhail V. Andreev Maxim V. Musalov Irina V. Sterkhova Svetlana V. Amosova Lyudmila I. Larina |
| author_sort | Vladimir A. Potapov |
| collection | DOAJ |
| description | The efficient regio- and stereoselective syntheses of (Z,Z)-bis(3-amino-3-oxo-1-propenyl) selenides and diselenides in high yields based on the nucleophilic addition of sodium selenide to 2-propynamides and sodium diselenide to 3-(trimethylsilyl)-2-propynamides have been developed. The first examples of the addition of a selenium-centered nucleophile to 2-propynamides with a terminal triple bond and diselenide anion to 3-(trimethylsilyl)-2-propynamides have been carried out. Bis(3-amino-3-oxo-1-propenyl) diselenides are a novel family of compounds, none of which has yet been described in the literature. The glutathione peroxidase-like activity of the obtained compounds has been evaluated and products with high activity have been found. It was established that diselenides are superior to selenides with the same substituents in glutathione peroxidase-like activity. The results of the structural studying of products by single-crystal X-ray diffraction analysis and <sup>77</sup>Se-NMR data are discussed. |
| first_indexed | 2024-03-09T23:30:24Z |
| format | Article |
| id | doaj.art-9d23753070a349b79340928a9e981a7f |
| institution | Directory Open Access Journal |
| issn | 2304-6740 |
| language | English |
| last_indexed | 2024-03-09T23:30:24Z |
| publishDate | 2022-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Inorganics |
| spelling | doaj.art-9d23753070a349b79340928a9e981a7f2023-11-23T17:10:27ZengMDPI AGInorganics2304-67402022-05-011067410.3390/inorganics10060074Regio- and Stereoselective Synthesis of (Z,Z)-Bis(3-amino-3-oxo-1-propenyl) Selenides and Diselenides Based on 2-propynamides: A Novel Family of Diselenides with High Glutathione Peroxidase-like ActivityVladimir A. Potapov0Mikhail V. Andreev1Maxim V. Musalov2Irina V. Sterkhova3Svetlana V. Amosova4Lyudmila I. Larina5A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, RussiaThe efficient regio- and stereoselective syntheses of (Z,Z)-bis(3-amino-3-oxo-1-propenyl) selenides and diselenides in high yields based on the nucleophilic addition of sodium selenide to 2-propynamides and sodium diselenide to 3-(trimethylsilyl)-2-propynamides have been developed. The first examples of the addition of a selenium-centered nucleophile to 2-propynamides with a terminal triple bond and diselenide anion to 3-(trimethylsilyl)-2-propynamides have been carried out. Bis(3-amino-3-oxo-1-propenyl) diselenides are a novel family of compounds, none of which has yet been described in the literature. The glutathione peroxidase-like activity of the obtained compounds has been evaluated and products with high activity have been found. It was established that diselenides are superior to selenides with the same substituents in glutathione peroxidase-like activity. The results of the structural studying of products by single-crystal X-ray diffraction analysis and <sup>77</sup>Se-NMR data are discussed.https://www.mdpi.com/2304-6740/10/6/74divinyl diselenidesdivinyl selenidespropynamidesglutathione peroxidase-like activityseleniumsodium diselenide |
| spellingShingle | Vladimir A. Potapov Mikhail V. Andreev Maxim V. Musalov Irina V. Sterkhova Svetlana V. Amosova Lyudmila I. Larina Regio- and Stereoselective Synthesis of (Z,Z)-Bis(3-amino-3-oxo-1-propenyl) Selenides and Diselenides Based on 2-propynamides: A Novel Family of Diselenides with High Glutathione Peroxidase-like Activity Inorganics divinyl diselenides divinyl selenides propynamides glutathione peroxidase-like activity selenium sodium diselenide |
| title | Regio- and Stereoselective Synthesis of (Z,Z)-Bis(3-amino-3-oxo-1-propenyl) Selenides and Diselenides Based on 2-propynamides: A Novel Family of Diselenides with High Glutathione Peroxidase-like Activity |
| title_full | Regio- and Stereoselective Synthesis of (Z,Z)-Bis(3-amino-3-oxo-1-propenyl) Selenides and Diselenides Based on 2-propynamides: A Novel Family of Diselenides with High Glutathione Peroxidase-like Activity |
| title_fullStr | Regio- and Stereoselective Synthesis of (Z,Z)-Bis(3-amino-3-oxo-1-propenyl) Selenides and Diselenides Based on 2-propynamides: A Novel Family of Diselenides with High Glutathione Peroxidase-like Activity |
| title_full_unstemmed | Regio- and Stereoselective Synthesis of (Z,Z)-Bis(3-amino-3-oxo-1-propenyl) Selenides and Diselenides Based on 2-propynamides: A Novel Family of Diselenides with High Glutathione Peroxidase-like Activity |
| title_short | Regio- and Stereoselective Synthesis of (Z,Z)-Bis(3-amino-3-oxo-1-propenyl) Selenides and Diselenides Based on 2-propynamides: A Novel Family of Diselenides with High Glutathione Peroxidase-like Activity |
| title_sort | regio and stereoselective synthesis of z z bis 3 amino 3 oxo 1 propenyl selenides and diselenides based on 2 propynamides a novel family of diselenides with high glutathione peroxidase like activity |
| topic | divinyl diselenides divinyl selenides propynamides glutathione peroxidase-like activity selenium sodium diselenide |
| url | https://www.mdpi.com/2304-6740/10/6/74 |
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