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N-aryl benzisoselenazolones – synthesis, transformations and antioxidant activity
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1  Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland


The applicability of organoselenium compounds in medicinal chemistry arises from their unique biological properties, among which the antioxidant activity seems to be the leading one. Since ebselen (N-phenyl-1,2-benzisoselenazol-3(2H)-one) has been proven to mimic the activity of the antioxidant enzyme glutathione peroxidase GPx, the search for more effective peroxide scavengers has become a ‘hot topic’ in this field of research. Herein, we present the synthesis of N-aryl ebselen derivatives, bearing additional electron donating or electron withdrawing groups in the N-phenyl ring, by two methods: (a) reaction of N-substituted o-iodobenzamides with lithium diselenide, (b) synthesis based on the formation of 2,2-diselenobis(benzoic acid), followed by the conversion to corresponding dichloride and further reaction with amine. Significant improvements in these methodologies are highlighted. All obtained ebselen derivatives were further converted to corresponding diselenides by the treatment with sodium borohydride. The antioxidant potential of the obtained selenium derivatives and conclusions concerning the activity-structure relation are presented.

Keywords: ebselen, benzisoselenazol-3(2H)-ones, diselenides, antioxidant activity
Comments on this paper
Claudio Santi
antioxidant activity
There are 2 ebselen like structure that seems to have really a powerful GPx-Like acticvity the same trends is not respected for the analogous diselenides. In addition using the Iwaoka methods the kinetic of DTT oxiddations are normally very long and T50 is used as comparison parameter. In the case in which the oxidation is complete after 5 minutes did you confirm this data for 2 or more time? I experimented that sometime thhis method failed affording apparently fast reaction for not very well detectable reasons.

Thanks a lot and congratulation for the nice data
Jacek Ścianowski
Thank you for your comment. We have used Iwaoka methodology as a standard procedure to check GPx-like acticvity. Of course we have repeated all experiments 2-3 times. We have not had any problems with this method.