Synthesis of 2H,3-4-Dihydro-1,2-benzoselenazin-3-one and derivatives : A new heterocyclic ring system.

Jacquemin, P.; Christiaens, L.; Renson, M.; Evers, M.; Dereu, N.

doi:10.1016/s0040-4039(00)74805-2

Cited by 88 publications

(30 citation statements)

References 15 publications

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“…[3] These mimics include the well-known anti-inflammatory compound ebselen (1) [4] and its analogues, [5,6] camphor-based selenenyl amide 2, [7] tert-amino-substituted diselenides 3-7,…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure–Activity Correlation Studies of Secondary‐ and Tertiary‐Amine‐Based Glutathione Peroxidase Mimics

Bhabak¹,

Mugesh²

2009

Chemistry A European J

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In this study, a series of secondary- and tertiary-amino-substituted diaryl diselenides were synthesized and studied for their glutathione peroxidase (GPx) like antioxidant activities with H(2)O(2), cumene hydroperoxide, or tBuOOH as substrates and with PhSH or glutathione (GSH) as thiol cosubstrates. This study reveals that replacement of the tert-amino groups in benzylamine-based diselenides by sec-amino moieties drastically enhances the catalytic activities in both the aromatic thiol (PhSH) and GSH assay systems. Particularly, the N-propyl- and N-isopropylamino-substituted diselenides are 8-18 times more active than the corresponding N,N-dipropyl- and N,N-diisopropylamine-based compounds in all three peroxide systems when GSH is used as the thiol cosubstrate. Although the catalytic mechanism of sec-amino-substituted diselenides is similar to that of the tert-amine-based compounds, differences in the stability and reactivity of some of the key intermediates account for the differences in the GPx-like activities. It is observed that the sec-amino groups are better than the tert-amino moieties for generating the catalytically active selenols. This is due to the absence of any significant thiol-exchange reactions in the selenenyl sulfides derived from sec-amine-based diselenides. Furthermore, the seleninic acids (RSeO(2)H) derived from the sec-amine-based compounds are more stable toward further reactions with peroxides than their tert-amine-based analogues.

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“…[3] These mimics include the well-known anti-inflammatory compound ebselen (1) [4] and its analogues, [5,6] camphor-based selenenyl amide 2, [7] tert-amino-substituted diselenides 3-7,…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure–Activity Correlation Studies of Secondary‐ and Tertiary‐Amine‐Based Glutathione Peroxidase Mimics

Bhabak¹,

Mugesh²

2009

Chemistry A European J

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“…6 The mode of the biological action of ebselen and its analogues has been postulated to be similar to that observed for GSH-Px and results in dehydrogenation of thiols to disulfides while hydrogen peroxide is reduced to water. 7,41 Later it was found that ebselen did not promote hydrogen peroxide oxidation of thiols such as N-acetylcysteine, butanethiol and octanethiol in nonenzymic conditions. 42 Nevertheless, the selenenamide derived from camphor effectively catalyzed oxidation of phenylmethanethiol to the disulfide.…”

Section: Oxidation Of Organosulfur Compoundsmentioning

confidence: 99%

“…43 The postulated mechanism of the enzyme-like action of ebselen is presented in Scheme 18. 7,41,43,44 When concentration of hydroperoxide is high, ebselen (13) is oxidized to selenoxide 69 which reacting with one molecule of the thiol gives selenosulfide 70. The intermediate 70 and the second molecule of thiol produce disulfide while the selenenic acid 71 is converted back to the ebselen.…”

Section: Oxidation Of Organosulfur Compoundsmentioning

confidence: 99%

Diaryl diselenides and benzisoselenazol-3(2H)-ones as oxygen-transfer agents

Młochowski¹,

Brzaszcz²,

Chojnacka³

et al. 2004

Arkivoc

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Diaryl diselenides and related benzisoselenazol-3(2H)-ones are presented as the catalyst for hydogen peroxide and t-butylhydroperoxide oxidation of various types of organic substrates. Most of the reactions studied in our laboratory have a practical value. The aromatic aldehydes and ketones are oxidized to arenecarboxylic acids or converted to the phenols while cycloalkanones gave cycloalkanecarboxylic acids with ring contraction. From the azomethine compounds, depending on their structure, nitriles, parent carbonyl compounds, carboxylic acids or their esters are produced. Primary benzylamines gave nitriles, while the secondary are oxidized to nitrones. Alkylarenes are oxidized to the alkylaryl ketones and alkenes to epoxides. By oxidation of 1,4-dimethoxysubstituted and some polycondensed arenes the quinones are produced. The postulated mechanisms are discussed and the methods for synthesis of the title compounds are described.

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“…Hence, the design, synthesis, and evaluation of small-molecule selenium compounds that mimic the biological activity of GPx have been investigated by several groups, and selected examples 2 [28], 3 [29], 4 [30], and 5 [31] are presented in Scheme 2. Various diaryl diselenides [32][33][34][35][36][37][38] and certain types of tellurium compounds as well as dendrimeric and cyclodextrin-derived organochalcogen catalysts that emulate GPx have also been reported [39][40][41][42][43][44][45][46].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of a New Five and Six Membered Selenoheterocyclic Compounds Homologues of Ebselen

Messali

Abboudi

Aouad

et al. 2011

Organic Chemistry International

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The discovery of the antioxidant activity of selenoenzyme glutathione peroxidase (GPx) has attracted growing attention in the biochemistry of selenium. Among molecules which mimic the structure of the active site of the enzyme, N-phenyl-1,2-benzisoselenazolin-3-one 1, Ebselen, exhibited useful anti-inflammatory properties. It has been extensively investigated and has undergone clinical trials as an anti-inflammatory agent. Unfortunately, Ebselen exhibits relatively poor catalytic activity, prompting attempts to design more efficacious GPx mimetics that would retain his low toxicity while manifesting improved catalytic properties. In this context, novel 1,2-benzoselenazine and 1,2-benzoselenazols, which are five and six membered homologues of Ebselen were synthesized and characterized. One structure has been proven by single crystal X-ray crystallography.

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Synthesis of 2H,3-4-Dihydro-1,2-benzoselenazin-3-one and derivatives : A new heterocyclic ring system.

Cited by 88 publications

References 15 publications

Synthesis and Structure–Activity Correlation Studies of Secondary‐ and Tertiary‐Amine‐Based Glutathione Peroxidase Mimics

Synthesis and Structure–Activity Correlation Studies of Secondary‐ and Tertiary‐Amine‐Based Glutathione Peroxidase Mimics

Diaryl diselenides and benzisoselenazol-3(2H)-ones as oxygen-transfer agents

Synthesis and Characterization of a New Five and Six Membered Selenoheterocyclic Compounds Homologues of Ebselen

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