121st General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Event Hall
Time 4월 19일 (목요일) 11:00~12:30
Code ORGN.P-570
Subject Synthesis and Anticancer Evaluation of 2,3-Disubstituted Indoles Derived from Azobenzenes via Rh(III)-Catalyzed C-H Activation
Authors Saegun Kim, IN SU KIM1,*
Sungkyunkwan University, Korea
1College of Pharmacy / Department of Pharmacy, Sungkyunkwan University, Korea
Abstract The azo-directed rhodium(III)-catalyzed C−H functionalization and intramolecular annulations between azobenzenes and internal olefins are described. This transformation provides efficient preparation of 2,3-disubstituted free-(NH)-indoles with excellent site-selectivity and functional group compatibility. The synthetic compounds 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). Synthesized 2,3-disubstituted indoles were found to display potent cytotoxic effect competitive with anticancer agent doxorubicin. In sharp contrast, we herein reported the formation of 2,3-disubstituted indoles through the Rh(III)-catalyzed cross-coupling reaction of azobenzenes and internal olefins such as maleates and fumarates. Furthermore, synthesized 2,3-disubstituted indole derivatives have been evaluated for the cytotoxic effect against human endometrial adenocarcinoma cells (Ishikawa), triple negative human breast cancer cells (MDA-MB-231) and human renal cancer cells (Caki-1), and were found to have promising anticancer properties competitive with anticancer agent doxorubicin.
E-mail jameskim1991@naver.com