Click Chemistry of Selenium Dihalides: Novel Bicyclic Organoselenium Compounds Based on Selenenylation/Bis-Functionalization Reactions and Evaluation of Glutathione Peroxidase-like Activity

• Published in: International journal of molecular sciences Vol. 23; no. 24; p. 15629
• Main Authors: Musalov, Maxim V, Potapov, Vladimir A
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 09.12.2022; MDPI
• Subjects: 9-selenabicyclo[3.3.1]nonane derivatives; Acetylene; Aging; Alcohol; Alcohols; Alkynes - chemistry; Anions; Biological activity; Chemistry; Click Chemistry; Clinical trials; Coronaviruses; Cycloaddition; Enzymes; Glutathione Peroxidase; glutathione peroxidase-like activity; Immunization; Laboratories; Lipid peroxidation; Lipids; Metabolism; Nonanes; Organoselenium compounds; Organoselenium Compounds - chemistry; Oxidative stress; Peroxidase; Phenols; Propargyl alcohol; Reagents; Selenium; Selenium - chemistry; Selenium Compounds - chemistry; selenium dihalides; Sodium; Stroke; Vaccines; Vitamin E; alcohols; glutathione peroxidase-like activity; 9-selenabicyclo[3.3.1]nonane derivatives; selenium dihalides
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms232415629

A number of highly efficient methods for the preparation of novel derivatives of 9-selenabicyclo[3.3.1]nonane in high yields based on selenium dibromide and cis,cis-1,5-cyclooctadiene are reported. The one-pot syntheses of 2,6-diorganyloxy-9-selenabicyclo[3.3.1]nonanes using various O-nucleophiles including alkanols, phenols, benzyl, allyl, and propargyl alcohols were developed. New 2,6-bis(1,2,3-triazol-1-yl)-9-selenabicyclo[3.3.1]nonanes were obtained by the copper-catalyzed 1,3-dipolar cycloaddition of 2,6-diazido-9-selenabicyclo[3.3.1]nonane with unsubstituted gaseous acetylene and propargyl alcohol. The synthesis of 2,6-bis(vinylsulfanyl)-9-selenabicyclo[3.3.1]nonane, based on the generation of corresponding dithiolate anion from bis[amino(iminio)methylsulfanyl]-9-selenabicyclo[3.3.1]nonane dibromide, followed by the nucleophilic addition of the dithiolate anion to unsubstituted acetylene, was developed. The glutathione peroxidase-like activity of the obtained water-soluble products was estimated and compounds with high activity were found. Overall, 2,6-Diazido-9-selenabicyclo[3.3.1]nonane exhibits the highest activity among the obtained compounds.