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Issue 35, 2019
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Copper complexes and carbon nanotube–copper ferrite-catalyzed benzenoid A-ring selenation of quinones: an efficient method for the synthesis of trypanocidal agents

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Abstract

We report a new method for A-ring selenation of naphthoquinones and anthraquinones and discuss the relevant trypanocidal activity of the synthesized compounds. We have demonstrated three efficient strategies for the preparation of the target selenium derivatives, i.e. (a) copper(I) thiophene-2-carboxylate and in situ generated Santi's reagent were used to prepare selenium-substituted benzenoid quinones, (b) copper complexes and (c) carbon nanotube-supported copper ferrite as catalysts in the presence of AgSeR-salts were also used for the synthesis of selenium-containing quinoidal derivatives. These new methods provide efficient and practical strategies for the preparation of selenium-based quinones. In addition, we have discovered nine compounds with potent trypanocidal activity. The derivatives 2a–2e showed potent trypanocidal activity with IC50 values in the range of 13.3 to 37.0 μM.

Graphical abstract: Copper complexes and carbon nanotube–copper ferrite-catalyzed benzenoid A-ring selenation of quinones: an efficient method for the synthesis of trypanocidal agents

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Publication details

The article was received on 19 Apr 2019, accepted on 25 Jul 2019 and first published on 25 Jul 2019


Article type: Paper
DOI: 10.1039/C9NJ02026H
New J. Chem., 2019,43, 13751-13763

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    Copper complexes and carbon nanotube–copper ferrite-catalyzed benzenoid A-ring selenation of quinones: an efficient method for the synthesis of trypanocidal agents

    G. A. M. Jardim, Í. A. O. Bozzi, W. X. C. Oliveira, C. Mesquita-Rodrigues, R. F. S. Menna-Barreto, R. A. Kumar, E. Gravel, E. Doris, A. L. Braga and E. N. da Silva Júnior, New J. Chem., 2019, 43, 13751
    DOI: 10.1039/C9NJ02026H

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