- Nucleophilic cleavage of selenaheterocyclic ring in benzisoselenazol-3(2H)- ones and 1,3,2-benzodiselenazoles
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The reactions of cyclic selenenamides: benzisoselenazol-3(2H)-ones and 1,3,2-benzo-diselenazoles 3 with living cell nucleophiles such as water and thiols were investigated. Both of them caused Se-N bond cleavage. The thiolysis of 1 led to selenosulphides
- Lisiak,Mlochowski,Palus
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p. 1403 - 1411
(2008/09/17)
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- Formation of Thiocarbonyl Compounds in the Reaction of Ebselen Oxide with Thiols
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Reaction of α-toluenethiol with Ebselen oxide, 2, affords dibenzyl disulfide and seleno sulfide 5, R = PhCH2.In the course of this reaction, thiobenzaldehyde is formed and can be trapped with cyclopentadiene in 90percent yield.Reaction of 2-propene-1-thiol with 2 afforded thioacrolein dimer in 69percent yield and seleno sulfide 5, R = CH2-CH=CH2.Trapping, stereochemical, and isotopic exchange studies were used to determine if in the reaction of 2 with 1-heptanethiol, cyclohexanethiol, and N-acetyl-D,L-cysteine thiocarbonyl compounds heptanethial, cyclohexanethione, and 2-acetamino-3-thioxopropanoic acid (α-thioformyl-N-acetylglycine), respectively, are also formed.These studies showed that free thiocarbonyl compounds are not formed in these reactions.
- Glass, Richard S.,Farooqui, Firdous,Sabahi, Mahmood,Ehler, Kenneth W.
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p. 1092 - 1097
(2007/10/02)
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- MECHANISM OF THE CATALYTIC REDUCTION OF HYDROPEROXIDES BY EBSELEN : A SELENIUM - 77 NMR STUDY
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Ebselen (2-phenyl-1,2-benzisoselenazol-3(2H)-one 1, a non-toxic selenium containing heterocyclic compound has been shown to display both anti-inflammatory activity in vivo and GSH-Px-like activity in vitro.Using (1)H and (77)Se NMr we investigated the mechanism of reduction of hydroperoxides by thiols in the presence of 1.A catalytic cycle depending on the formation of diselenides and selenylsulfides was found.The selenic acid oxidation level present in compound 1 is particularly stable because of the intermolecular cyclisation.This contracts with previously reported results concerning the oxidation of organoselenium compounds.
- Fisher, Hartmut,Dereu, Norbert
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p. 757 - 768
(2007/10/02)
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