Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 20, Pages 3832-3837Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob00157k
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Funding
- National Natural Science Foundation of China [21861006, 21961042]
- Guangxi Natural Science Foundation of China [2016GXNSFEA380001, 2018GXNSFBA281151]
- Guangxi Key RD Program [AB18221005]
- Science and Technology Major Project of Guangxi [AA17204058-21]
- Guangxi Science and Technology Base and Special Talents [guike AD19110027]
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources [CMEMR2019-A03]
- Innovation Project of Guangxi Graduate Education [YCBZ2019030]
- National College Students Innovation and Entrepreneurship Training Program [201910602019]
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An environmentally benign electrochemically enabled site-selective functionalization of indole or aniline derivatives with hexafluoroisopropanol in the presence of tetrabutyl ammonium hexafluorophosphate as the redox catalyst and electrolyte was demonstrated in this work. Under mild electro-oxidation conditions, a series of hexafluoroisopropoxy indole and aniline derivatives with pharmacological activity were obtained. This conversion does not need transition metals and oxidants, and has good functional group tolerance. The in vitro cytotoxicity of all compounds was evaluated by the MTT assay against four human cancer cell lines. The results revealed that hexafluoroisopropoxy indoles have good antitumor activity and compound 2i increased the intracellular levels of ROS and inhibited apoptosis in HeLa cells.
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