Selenium-containing quinone-based 1,2,3-triazoles were synthesized using click chemistry, the copper catalyzed azide-alkyne 1,3-dipolar cycloaddition, and evaluated against six types of cancer cell lines: HL-60 (human promyelocytic leukemia cells), HCT-116 (human colon carcinoma cells), PC3 (human prostate cells), SF295 (human glioblastoma cells), MDA-MB-435 (melanoma cells) and OVCAR-8 (human ovarian carcinoma cells). Some compounds showed IC50 values < 0.3 μM. The cytotoxic potential of the quinones evaluated was also assayed using non-tumor cells, exemplified by peripheral blood mononuclear (PBMC), V79 and L929 cells. Mechanistic role for NAD(P)H:Quinone Oxidoreductase 1 (NQO1) was also elucidated. These compounds could provide promising new lead derivatives for more potent anticancer drug development and delivery, and represent one of the most active classes of lapachones reported.

Electrochemical selenation in undivided electrochemical cells allows the preparation of selenium‐containing naphthoquinones. The rapid, green and efficient protocol avoids chemical oxidants and enables the synthesis of target molecules in a fast and reliable way. This strategy provides and efficient and general method for the synthesis of quinoidal compounds with activity against five cancer cell lines and Trypanosoma cruzi, the parasite that causes Chagas disease.

Rh-catalyzed C-5 selective C–H iodination of naphthoquinones provides a gateway to previously inaccessible A-ring analogues. C-2 selective processes can be achieved under related conditions.