Issue 35, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
19 Eph 2019
Accepted
25 Jul 2019
First published
25 Jul 2019

New J. Chem., 2019,43, 13751-13763

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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