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Molecules 2018, 23(1), 83; doi:10.3390/molecules23010083

Synthesis of Selenium-Quinone Hybrid Compounds with Potential Antitumor Activity via Rh-Catalyzed C-H Bond Activation and Click Reactions

Department of Chemistry, Institute of Exact Sciences, Federal University of Minas Gerais, UFMG, 31270-901 Belo Horizonte, Brazil
Division of Bioorganic Chemistry, Department of Pharmacy, University of Saarland, Campus B2 1, D-66123 Saarbruecken, Germany
Department of Physiology and Pharmacology, Federal University of Ceará, CEP 60180-900 Fortaleza, Brazil
Department of Chemistry, Federal University of Santa Catarina, 88040-900 Florianópolis, Brazil
Authors to whom correspondence should be addressed.
Received: 16 November 2017 / Revised: 16 December 2017 / Accepted: 22 December 2017 / Published: 30 December 2017
(This article belongs to the Special Issue Small Molecule Catalysts with Therapeutic Potential)
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In continuation of our quest for new redox-modulating catalytic antitumor molecules, selenium-containing quinone-based 1,2,3-triazoles were synthesized using rhodium-catalyzed C-H bond activation and click reactions. All compounds were evaluated against five types of cancer cell lines: HL-60 (human promyelocytic leukemia cells), HCT-116 (human colon carcinoma cells), SF295 (human glioblastoma cells), NCIH-460 (human lung cells) and PC3 (human prostate cancer cells). Some compounds showed good activity with IC50 values below 1 µM. The cytotoxic potential of the naphthoquinoidal derivatives was also evaluated in non-tumor cells, exemplified by L929 cells. Overall, these compounds represent promising new lead derivatives and stand for a new class of chalcogenium-containing derivatives with potential antitumor activity. View Full-Text
Keywords: lapachol; naphthoquinone; cancer; selenium; click chemistry; C-H activation lapachol; naphthoquinone; cancer; selenium; click chemistry; C-H activation

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Jardim, G.A.M.; Lima, D.J.B.; Valença, W.O.; Lima, D.J.B.; Cavalcanti, B.C.; Pessoa, C.; Rafique, J.; Braga, A.L.; Jacob, C.; da Silva Júnior, E.N.; da Cruz, E.H.G. Synthesis of Selenium-Quinone Hybrid Compounds with Potential Antitumor Activity via Rh-Catalyzed C-H Bond Activation and Click Reactions. Molecules 2018, 23, 83.

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