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Nitro-, Azo-, and A...
Nitro-, Azo-, and Amino Derivatives of Ebselen : Synthesis, Structure, and Cytoprotective Effects
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- Singh, Vijay P. (författare)
- Uppsala universitet,Institutionen för kemi - BMC
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- Poon, Jia-fei (författare)
- Uppsala universitet,Institutionen för kemi - BMC
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- Yan, Jiajie (författare)
- Uppsala universitet,Institutionen för kemi - BMC
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- Lu, Xi (författare)
- Uppsala universitet,Tillämpad materialvetenskap
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- Karlsson Ott, Marjam (författare)
- Uppsala universitet,Tillämpad materialvetenskap
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- Butcher, Ray J. (författare)
- Howard Univ, Dept Chem, Washington, DC 20059 USA
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- Gates, Paul J. (författare)
- Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
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- Engman, Lars (författare)
- Uppsala universitet,Institutionen för kemi - BMC
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(creator_code:org_t)
- 2016-12-20
- 2017
- Engelska.
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Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 82:1, s. 313-321
- Relaterad länk:
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https://research-inf...
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- Novel azo-bis-ebselen compounds 7 were prepared by reduction of 7-nitro-2-aryl-1,2-benzisoselenazol-3(2H)ones 3 and 6 with sodium benzenetellurolate; NaTeC6H5, and by reaction of 2-bromo-3-nitrobenzamides with Na2Se2. The X-ray structure of 7b showed that the molecule, due to strong intramolecular secondary Se center dot center dot center dot N interactions, is completely planar. Azo-compounds 7 upon further reaction with NaTeC6H5 were reductively cleaved to provide 2 equiv of the corresponding aromatic amine. The weak Se-N bond was not stable enough to survive the reaction conditions, and diselenides 8 were isolated after workup. Whereas azo-bis-ebselens 7 were poor mimics of the glutathione peroxidase (GPx)-enzymes, nitroebselens 3, 6, and 11b and diselenides 8 were 3-6-fold more active than ebselen. Based on Se-77 NMR. spectroscopy, a catalytic cycle for diselenide 8b, involving aminoebselen 14, was proposed. As assessed by chemiluminescence measurements, the good GPx-mimics could reduce production of reactive oxygen species (ROS) in stimulated human mononuclear cells more efficiently than Trolox. No toxic effects of the, compounds were seen in MC3T3-cells at 25 mu M.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
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