4.6 Article

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

Journal

MOLECULES
Volume 23, Issue 1, Pages -

Publisher

MDPI
DOI: 10.3390/molecules23010083

Keywords

lapachol; naphthoquinone; cancer; selenium; click chemistry; C-H activation

Funding

  1. Conselho Nacional de Desenvolvimento Cientifico e Tecnologico [CNPq 305385/2014-3, PVE 401193/2014-4, 477346/2013-8, 01/2016, APQ-02478-14]
  2. Programa Pesquisador Mineiro [PPM-00638-16]
  3. INCT-Catalise
  4. CAPES

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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 mu M. 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.

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