106663-83-6

Upstream product

• 1441-85-6 2-(chloroseleno)benzoyl chloride 
• 171977-70-1 2-(benzylseleno)-N-tert-butylbenzamide 
• 153871-79-5 2-tert-butyl-1,2-benzisoselenazol-3(2H)-one 1-oxide 
• 106663-99-4 2-(tert-butyl)benzo[d][1,2]selenazol-3(2H)-one 

Relevant academic research and scientific papers

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.

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.

Aromatic and Azaaromatic Diselenides, Benzisoselenazolones and Related Compounds as Immunomodulators Active in Humans: Synthesis and Properties

Convenient syntheses of aryl diselenides 2, 1,2-benzisoselenazol-3(2H)-ones 4 and their 1-oxides 7 are reported.Reductive conversions of these compounds to bis(2-carbamoyl)phenyl diselenides 5 and oxidative cyclization of 5 to 1,2-benzisoselenazol-3(2H)-one 1-oxides 7 as the methods for the synthesis of these compounds are reported.Their ability to induce cytokines, such as TNF and IFN-γ, in human peripheral blood leucocyte cultures is described. - Key Words: 1,2-benzisoselenazol-3(2H)-ones/ Cytokine inducers/ Diselenides/ Interferon-gamma/ Tumor necrosis factor

Diselenobis-benzoic acid amides of primary and secondary amines and processes for the treatment of diseases in humans caused by a cell injury

The present invention relates to new diselenobis-benzoic acid amides of primary and secondary amines of the general formula (I): STR1 and processes for the treatment of diseases in humans caused by a cell injury.