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Nitro-, Azo-, and Amino Derivatives of Ebselen: Synthesis, Structure, and Cytoprotective Effects
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Applied Materials Sciences.
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2017 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, no 1, p. 313-321Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2017. Vol. 82, no 1, p. 313-321
National Category
Organic Chemistry Engineering and Technology
Identifiers
URN: urn:nbn:se:uu:diva-312514DOI: 10.1021/acs.joc.6b02418ISI: 000391781900030PubMedID: 27966348OAI: oai:DiVA.org:uu-312514DiVA, id: diva2:1063681
Funder
ÅForsk (Ångpanneföreningen's Foundation for Research and Development), 16-364Stiftelsen Olle Engkvist Byggmästare, 2016/159Carl Tryggers foundation , CTS 13:346Available from: 2017-01-10 Created: 2017-01-10 Last updated: 2017-11-29Bibliographically approved

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Singh, Vijay P.Poon, Jia-feiYan, JiajieLu, XiKarlsson Ott, Marjam

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