scholarly journals (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

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5940
Author(s):  
Mikhail V. Andreev ◽  
Vladimir A. Potapov ◽  
Maxim V. Musalov ◽  
Svetlana V. Amosova
Keyword(s):  
Glutathione Peroxidase ◽  
Stereoselective Synthesis ◽  
Model Reaction ◽  
Amide Group ◽  
Organoselenium Compounds ◽  
Stereoselective Reaction ◽  
Very High

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.

scholarly journals Synthetic Approaches to Organoselenium Derivatives with Antimicrobial and Anti-Biofilm Activity

2019 ◽  
Vol 16 (6) ◽  
pp. 589-601 ◽  
Author(s):  
Iris Di Leo ◽  
Federica Messina ◽  
Vanessa Nascimento ◽  
Francesca G. Nacca ◽  
Donatella Pietrella ◽  
...  
Keyword(s):  
Glutathione Peroxidase ◽  
Biological Activities ◽  
Antimicrobial Activities ◽  
Pharmacological Properties ◽  
Organoselenium Compounds ◽  
Synthetic Approaches ◽  
First Time

In the recent years, an increasing attention has been given to the biological activities exerted by organoselenium compounds. In 1984, Sies reported for the first time the ability of ebselen to mimic the activity of glutathione peroxidase. From this milestone, several studies reported the pharmacological properties of selenium-containing compounds including their exploitation as antimicrobials. In this context, this minireview presents the most recent examples of seleno derivatives endowed with antimicrobial activities while discussing the most interesting and recent synthetic procedures used to obtain these compounds.

scholarly journals Seleninic Acid Potassium Salts as Water-Soluble Biocatalysts with Enhanced Bioavailability

Materials ◽  
2020 ◽  
Vol 13 (3) ◽  
pp. 661 ◽  
Author(s):  
Magdalena Obieziurska ◽  
Agata J. Pacuła ◽  
Anna Laskowska ◽  
Angelika Długosz-Pokorska ◽  
Anna Janecka ◽  
...  
Keyword(s):  
Glutathione Peroxidase ◽  
Anticancer Agents ◽  
Potassium Salt ◽  
Water Soluble ◽  
Potassium Salts ◽  
Organoselenium Compounds ◽  
Protic Solvents ◽  
Ros Formation ◽  
Mcf 7 ◽  
Acid Salts

Organoselenium compounds are well-known glutathione peroxidase (GPx) mimetics that possess antioxidants/prooxidant properties and are able to modulate the concentration of reactive oxygen species (ROS), preventing oxidative stress in normal cells or inducing ROS formation in cancer cells leading to apoptosis. The purpose of this study was the synthesis of potent GPx mimics with antioxidant and anticancer activity along with improved bioavailability, as a result of good solubility in protic solvents. As a result of our research, glutathione peroxidase (GPx) mimetics in the form of water-soluble benzeneseleninic acid salts were obtained. The procedure was based on the synthesis of 2-(N-alkylcarboxyamido)benzeneselenenic acids, through the oxidation of benzisoselenazol-3(2H)-ones or analogous arenediselenides with an amido group, which were further converted to corresponding potassium salts by the treatment with potassium tert-butanolate. All derivatives were tested as potential antioxidants and anticancer agents. The areneseleninic acid salts were significantly better peroxide scavengers than analogous acids and the well-known organoselenium antioxidant ebselen. The highest activity was observed for the 2-(N-ethylcarboxyamido)benzeneselenenic acid potassium salt. The strongest cytotoxic effect against breast cancer (MCF-7) and human promyelocytic leukemia (HL-60) cell lines was found for 2-(N-cyclohexylcarboxyamido)benzeneselenenic acid potassium salt and the 2-(N-ethylcarboxyamido)benzeneselenenic acid, respectively. The structure–activity correlations, including the differences in reactivity of benzeneseleninic acids and corresponding salts were evaluated.

Comparative effects of selenium supplementation on the plasma selenium concentration and erythrocyte glutathione peroxidase activity in cattle and camels

1998 ◽  
Vol 67 (3) ◽  
pp. 461-466 ◽  
Author(s):  
M. Bengoumi ◽  
A. K. Essamadi ◽  
J. C. Tressol ◽  
J. P. Chacornac ◽  
B. Faye
Keyword(s):  
Glutathione Peroxidase ◽  
Peroxidase Activity ◽  
Selenium Concentration ◽  
Basal Diet ◽  
Glutathione Peroxidase Activity ◽  
Plasma Selenium ◽  
Selenium Metabolism ◽  
Mineral Supplementation ◽  
Very High ◽  
Plasma Selenium Concentration

AbstractAt an experimental farm, five camels and five cows were each given a similar basal diet for 6 months. They received oral trace element supplementation for 3 months (day 22 to 112) which included zinc, copper, selenium, manganese, iodine and cobalt and corresponded to twice the daily requirement generally recommended for cows. Plasma selenium concentrations were significantly lower in the camels (20 (s.e. 2) mg/l) compared with the cows (33 (s.e. 2) μg/l). The mineral supplementation induced a large increase in the plasma selenium concentration in the camels which reached 200 (s.e. 35) fig/l. In the cows, the increase was much smaller and did not go beyond 65 (s.e. 8) μg/l. Before supplementation the red blood cell glutathione peroxidase activity was similar in the camel and the cow varying between 4000 and 6000 IU per 100 g haemoglobin. In both species, this activity increased with mineral supplementation and remained very high even when mineral supplementation was stopped. The results suggested that selenium metabolism in camels is different from that in the cows.

Stereoselective Synthesis of Spiro-α-methylene-γ-lactams via Chiral Quaternary 3-Aminooxindole Adducts Accessed by Zn-Mediated Allylation of Sulfinyl Ketimines

Synthesis ◽  
2020 ◽  
Vol 52 (17) ◽  
pp. 2551-2562 ◽  
Author(s):  
Ravi P. Singh ◽  
V. U. Bhaskara Rao ◽  
Shashank Singh ◽  
Krishna N. Tripathi
Keyword(s):  
Single Crystal ◽  
Structure Analysis ◽  
Efficient Method ◽  
Good Yield ◽  
Stereoselective Synthesis ◽  
High Selectivity ◽  
X Ray ◽  
Relative Stereochemistry ◽  
Very High

An efficient method for the stereoselective synthesis of α-methylene-γ-lactams via quaternary 3-aminooxindoles with very high selectivity (up to 98% ee) is described. The methodology leads to the construction of sterically congested chiral quaternary 3-aminooxindole adducts in good yield and with moderate to excellent diastereoselectivity (dr up to 95:5). The relative stereochemistry of the chiral quaternary 3-aminooxindoles adduct and the spiro-α-methylene-γ-lactam was confirmed to be syn by single-crystal X-ray structure analysis. Furthermore, the α-methylene-γ-lactam was successfully transformed into a range of chiral synthons.

Stereoselective Synthesis of Secondary Alkyllithiums and Their Application to Stereoselective Cuprations or Intramolecular Carbolithiations for the Stereoselective Synthesis of Alkylidene­cyclobutanes

Synthesis ◽  
2016 ◽  
Vol 48 (19) ◽  
pp. 3141-3154 ◽  
Author(s):  
Kohei Moriya ◽  
Kuno Schwärzer ◽  
Konstantin Karaghiosoff ◽  
Paul Knochel
Keyword(s):  
Stereoselective Synthesis ◽  
Triethyl Phosphite ◽  
Significant Loss ◽  
Very High ◽  
Acylation Reactions

Secondary alkyllithium reagents were prepared stereoselectively via an iodo–lithium exchange by using tert-butyllithium. The resulting secondary alkyllithiums were converted directly into the corresponding alkylcopper reagents by transmetalation with copper(I) bromide–triethyl phosphite [CuBr·P(OEt)3] with retention of configuration and without significant loss of stereoselectivity. The resulting alkylcopper reagents were used for carbocupration or acylation reactions. In addition, a new intramolecular carbolithiation of secondary alkyllithium reagents possessing a remote alkyne moiety was also investigated, allowing the stereoselective production of alkylidenecylobutane derivatives with very high stereocontrol.

Construction of pH sensitive smart glutathione peroxidase (GPx) mimics based on pH responsive pseudorotaxanes

2020 ◽  
Vol 18 (16) ◽  
pp. 3125-3134
Author(s):  
Jiaxi Li ◽  
Wenlong Jia ◽  
Ganghui Ma ◽  
Xiaoyin Zhang ◽  
Shaojie An ◽  
...  
Keyword(s):  
Glutathione Peroxidase ◽  
Ph Sensitive ◽  
Ph Responsive ◽  
Organoselenium Compounds

Two pH-sensitive smart glutathione peroxidase (GPx) mimics were developed by using pH-responsive pseudorotaxanes based on cucurbit[6]uril and organoselenium compounds.

scholarly journals A General Synthetic Approach to Hydroquinone Meroterpenoids: Stereoselective Synthesis of (+)-(S)-Metachromin V and Alliodorol

2014 ◽  
Vol 9 (3) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Stefano Serra ◽  
Alessandra A. Cominetti ◽  
Veronica Lissoni
Keyword(s):  
Chemical Structure ◽  
Stereoselective Synthesis ◽  
Coupling Reaction ◽  
Protecting Groups ◽  
Magnesium Bromide ◽  
Synthetic Approach ◽  
Cross Coupling Reaction ◽  
New Synthesis ◽  
First Time ◽  
Very High

A new general synthetic approach to hydroquinone meroterpenoids is here described. The framework of the aforementioned natural compounds was built up through the Li2CuCl4 catalysed cross coupling reaction of the 4-substituted-( E)-prenyl acetates 9 with 2,5-bis(benzyloxy)phenyl magnesium bromide 8 as a key step. The latter sp3-sp2 coupling affords the products in good chemical yields and in very high stereoisomeric purity. A further key step of the present synthetic method consists of the removal of the benzylic protecting groups by a very mild procedure based on the use of lithium naphthalenide. The latter reagent, in combination with aliphatic dialkylamines, is able to cleave all the benzylic protecting groups leaving unaffected the polyenic moieties. By these means, we devised a new synthesis of the natural hydroquinone geranylhydroquinone, farnesylhydroquinone, metachromin V and alliodorol. In addition, the marine meroterpenoid, (+)-( S)-metachromin V, was synthesized for the first time; its chemical structure was confirmed and its absolute configuration was unambiguously assigned.

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