Synthesis and Anticancer Evaluation of 2, 3‐Disubstituted Indoles Derived from Azobenzenes and Internal Olefins. Issue 42 (1st September 2017)

• Record Type: Journal Article
• Authors: Oh, Yongguk; Han, Sang Hoon; Mishra, Neeraj Kumar; De, Umasankar; Lee, Junho; Kim, Hyung Sik; Jung, Young Hoon; Kim, In Su
• Is Part Of: European journal of inorganic chemistry. Issue 42(2017)
• Page Start: 6265
• Page End: 6273
• Publication Date: 2017-09-01
• Subjects: Cancer -- Azo compounds -- C‐H activation -- Indoles -- Nitrogen heterocycles -- Alkenes; Chemistry, Inorganic -- Periodicals; Organometallic chemistry -- Periodicals; Bioinorganic chemistry -- Periodicals; Solid state chemistry -- Periodicals; 546
• DOI: 10.1002/ejoc.201701001
• Languages: English
• ISSNs: 1434-1948

Abstract

Abstract : 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 indoles3b, 3k, and5b were found to show potent cytotoxic effects that were competitive with the anticancer agent doxorubicin. Abstract : Azo‐directed rhodium(III)‐catalysed C–H functionalization and intramolecular annulation reactions between azobenzenes and internal olefins are described. The resulting indoles were evaluated for in‐vitro anticancer activity against various human cancer cell lines.