60940-24-1

Usage

InChI:InChI=1/C14H13NOSe/c1-17-13-10-6-5-9-12(13)14(16)15-11-7-3-2-4-8-11/h2-10H,1H3,(H,15,16)

Upstream product

• 93-98-1 N-phenyl benzoyl amide 
• 74-88-4 methyl iodide 
• 106663-84-7 2,2‘-diselenobis(N-phenylbenzamide) 
• 110-05-4 di-tert-butyl peroxide 
• 1442-04-2 2-methylselenobenzoyl chloride 
• 62-53-3 aniline 
• 60940-34-3 2-phenyl-1,2-benzoisoselenazol-3(2H)-one 

Downstream Products

• 60940-41-2 benzo[d]isoselenazol-3-yl-phenyl-amine 
• 60975-10-2 3-chloro-2-phenyl-benzo[d]isoselenazolium; chloride 

Relevant academic research and scientific papers

Horseradish peroxidase inhibition and antioxidant activity of ebselen and related organoselenium compounds

Horseradish peroxidase (HRP) inhibition and glutathione peroxidase (GPx) activities of ebselen and some related derivatives are described. These studies show that ebselen and ebselen ditelluride (EbTe2) with significant antioxidant activity, inhibit the HRP-catalyzed oxidation reactions. In addition, inhibition of lipid peroxidation and singlet oxygen quenching studies were carried out. Although the inhibition of HRP by ebselen is comparable with that of EbTe2, the inhibitory effect on γ-radiation induced lipid peroxidation and the GPx activity of ebselen is found to be much higher than that of EbTe2.

Intramolecular homolytic substitution with amidyl radicals: A free-radical synthesis of ebselen and related analogues

Irradiation of a water-cooled benzene solution of pyridine-2-thioneoxycarbonyl (PTOC) imidate esters 9 derived from N-butyl-2-(benzylseleno)benzamide (6, R = Bu), 2-(benzylseleno)-N-hexylbenzamide (6, R = Hex), N-benzyl-2-(benzylseleno)benzamide (6, R = Bn), and 2-(benzylseleno)-N-cyclohexylbenzamide (6, R = c-Hex) with a 250-W low-pressure mercury lamp affords the corresponding 1,2-benzisoselenazol-3(2H)-ones (1) in yields of 81-91% (R = primary alkyl) and 45% (R = c-Hex). Presumably, these transformations involve formation of amidyl radicals 2 which undergo subsequent intramolecular homolytic substitution at the selenium atom with expulsion of a benzyl radical. PTOC imidate esters derived from 2-(benzylseleno)benzanilide (6, R = Ph) and 2-(benzylseleno)-N-tert-butylbenzamide (6, R = t-Bu) were unable to be prepared in this manner. 1,2-Benzisoselenazol-3(2H)-ones (1, R = Ph, Hex, i-Pr, t-Bu) could also be prepared in 76-85% yield by reaction of the corresponding 2,2'-diselenobis(benzamide) (15) with benzoyl or tert-butyl peroxide. The mechanisms of these transformations are discussed.

N-phenyl-2-(triphenylstannylseleno)benzamide and 2-methylseleno-N-phenylbenzamide

The two independent molecules of N-phenyl-2-(triphenylstannylseleno)benzamide, C31H25NOSeSn, differ significantly in the conformations of the N-phenylbenzamide groups. For 2-methylseleno-N-phenylbenzamide, C14H13/sub

Reactions of 2,2′-diselenobis(N-alkylbenzamides) with peroxides: A free-radical synthesis of ebselen and related analogues

N-Alkyl-2-triphenylstannylbenzamides (3, R = Hex, Ph, iso-Pro, tert-Bu), prepared from the corresponding 2-benzylselenobenzamides, react with benzoyl peroxide in benzene, under reflux, to afford the 2,2′-diselenobis(N-alkylbenzamides) (4) in 54-87% yield. Further treatment with benzoyl peroxide or di-tert-butyl peroxide in benzene or chlorobenzene affords the N-alkyl-1,2-benzisoselenazol-3(2H)-ones (2) in 76-85% yield. This transformation presumably involves intermediate amidyl radicals which undergo intramolecular homolytic substitution at selenium to afford the product.

SYNTHESES AND SPECTRAL CHARACTERIZATION OF THE METABOLITES OF A NEW ORGANO-SELENIUM DRUG: EBSELEN

The syntheses and spectral characterization of the metabolites of a new organo-selenium drug (ebselen) are described.

Photochemical Reaction of 2-Aryl-1,2-benzisoselenazol-3(2H)-ones

The photochemical reaction of 2-aryl-1,2-benzisoselenazol-3(2H)-ones (1) in benzene was found to give dibenzoselenazepin-11(10H)-ones (2).On the other hand, the photochemical reaction of 1 in t-butyl alcohol afforded 2-(2-hydroxy-2-methylpropylseleno)benzanilide, 2-(methylseleno)benzanilide, and 2-aryl-1,2-benzisoselenazol-3(2H)-one 1-oxides together with the photoisomer 2.Mechanisms for these reactions are proposed.