Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 1, Pages 313-321Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02418
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Funding
- Stiftelsen A-Forsk [16-364]
- Stiftelsen Olle Engkvist Byggmastare [2016/159]
- Carl Tryggers Stiftelse for Vetenskaplig Forskning [CTS 13:346]
- Engineering and Physical Sciences Research Council [EP/K03927X/1] Funding Source: researchfish
- EPSRC [EP/K03927X/1] Funding Source: UKRI
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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.
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