Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 42, Pages 6265-6273Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201701001
Keywords
Cancer; Azo compounds; C-H activation; Indoles; Nitrogen heterocycles; Alkenes
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Funding
- National Research Foundation of Korea (NRF) - Korea government (MSIP) [2016R1A4A1011189, 2017R1A2B2004786]
- National Research Foundation of Korea [2017R1A2B2004786, 2016R1A4A1011189] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Azo-directed rhodium(III)-catalysed C-H functionalization and intramolecular annulation reactions between azobenzenes and internal olefins are described. This transformation leads to 2,3-disubstituted free (NH)-indoles with excellent site-selectivity and functional-group compatibility. The resulting indoles were evaluated for in-vitro anticancer activity against human endometrial adenocarcinoma cells (Ishikawa), triple negative human breast cancer cells (MDA-MB-231), and human renal cancer cells (Caki-1). 2,3-Disubstituted indoles 3b, 3k, and 5b were found to show potent cytotoxic effects that were competitive with the anticancer agent doxorubicin.
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